The Great American Songbook - Sinatra Edition Quiz

Answer: That's Life

"You're ridin' high in April
Shot down in May
But I know I'm gonna change that tune
When I'm right back up on top in June..."

These lines from "That's Life" could certainly pertain to Frank Sinatra but they also were partly auto-biographical from the perspective of the 22 year old who wrote the lyric in 1962. Dean Kay had been trying to establish himself in music for a number of years when he finally appeared to be getting his big break that year. Some of his compositions were being published and recorded and the band he was with had just signed a recording contract itself. That was the "ridin' high in April". Shortly thereafter, he was drafted into the military and all the dreams were dashed - "shot down in May". That's when he and collaborator Kelly Gordon composed the song in about 20 minutes. But he did indeed bounce back eventually, not so much as an entertainer or composer but in the boardroom as COO or CEO of several record companies and musical entities such as ASCAP. That was his June.

Sinatra's variation of this calendar? Teen idol in the 1940s and then a career rupture in the early 1950s when he couldn't sing due to issues with his vocal cords and a declining popularity with the public because of his divorce from his first wife and his shenanigans with Ava Gardner. Those were his April and May. The June speaks for itself. He rehabilitated his career with an Oscar winning performance in "From Here to Eternity" and, under the musical direction of Nelson Riddle, recorded a raft of immensely popular albums over the next decade. He became "the" entertainer of the 20th Century.

Sinatra wasn't the first to record "That's Life". That honour would fall to jazz singer Marion Montgomery in 1964 followed by O.C. Smith in early 1966. Sinatra heard Smith's version while driving down the freeway one day, worked out a musical arrangement with Riddle and performed it on one of his TV specials.

Jimmy Bowen was the producer for the recording session a short time later. Sinatra arrived with wife Mia Farrow and an entourage of friends... they were on their way to a dinner engagement. After a couple of takes, Sinatra was satisfied with what he'd done and thought the session was over. Bowen indicated that if it was a hit they were after, what they had wouldn't do. He wanted another take. Sinatra wasn't pleased at all but finally relented and did it one more time. It growled in his anger and that's exactly what Bowen was after! When Sinatra heard the demo he immediately knew he had a hit and acknowledged that Bowen was responsible for setting the right tone to the recording. It rose to Number Four on Billboard's Hot 100 by December, 1966.

Sinatra tidbit - before recording this song, he met with O.C. Smith to seek his approval to do the cover.

Answer: You Make Me Feel So Young

Sinatra loved the uplifting energy that Riddle's arrangement imbued in this melody on the LP. He frequently sang it early in live performances to establish an ambiance for the evening utilizing an even punchier arrangement by Billy Byers rather than Riddle's. It's hard to say why this wasn't released as a single. Surely its ongoing popularity suggests it would have been a charting success but perhaps Haymes' so-so results in 1946 discouraged Capitol Records from releasing it for that purpose.

The tune was written by Josef Myrow, just another of the many talented Jewish emigres fleeing pre-revolution Russia. His family settled in Philadelphia and he was university trained to become a concert pianist. Along the way he started writing tunes for nightclub revues which ultimately led to work in Hollywood for the rest of his working days. This was his most enduring composition. The lyricist, Mack Gordon, was at the other end of the spectrum with a host of song writing credits to his name. Among his more memorable pieces were "At Last", "The More I See You", "I Can't Begin to Tell You", "Chattanooga Choo Choo" and "You'll Never Know". He was a favorite of Sinatra's.

Sinatra tidbits - 1. Sinatra sang this song at the youthful John F. Kennedy's presidential inauguration ceremony. 2. Frank, in interviews, would often state that one of the secrets to his success was that he tried to sing a song the way he perceived the lyricist wanted it to be done. And just how would he know that? By hanging out with them, naturally! They were among his favorite people and he would frequently drop in on them and discuss their works, or music in general, over a glass (or bottle) of bourbon. It's how he could interpret the soul of the song. It was also his habit to acknowledge and give credit to lyricists on stage.

Answer: the world

By the end of 1952, Frank Sinatra's career was in a shambles. His record label for the previous ten years, Columbia Records, did not renew his contract. His TV series was cancelled. He hadn't been cast in a movie for over a year. Live concert gigs had all but dried up and for the few he was booked, 300 people would show up in a hall that could hold ten times that. He was on the verge of bankruptcy! April 30th, 1953 was the red letter date when the great comeback commenced. He was about to begin a recording session for his new label, Capitol, but his old favorite Alex Stordahl was not conducting the orchestra. An earlier album with that combination had bombed and Capitol brought in a new guy to do the orchestrations. Gone were the lush string tinged ballads. The new sound was snappy and jazzy with horns. The first song, ironically, was "I've Got the World on a String", not exactly what Sinatra was feeling at the time but a song he had performed in concert occasionally. After finishing it up, Sinatra was reported to have asked "Who wrote that arrangement?" When advised it was the conductor, Nelson Riddle, he responded "That's beautiful... let's do another!" "South of the Border" was the second song put on vinyl that day and one of the greatest artist/arranger partnerships was born and it would last for well over a decade. Sinatra was turning a new page in his career!

"I've Got the World on a String" was written in 1932 by Harold Arlen and Ted Koehler, a combo who had hit pay dirt in 1930 with "Get Happy" and would later go on to compose "I Gotta Right to Sing the Blues" and "Stormy Weather" in 1933. Koehler related that he was lounging on a sofa one day when Arlen started working out the melody at the piano. He left the room with the tune in his head and returned a short time later with the lyric, it having just "dropped out of the sky". He modestly claimed that many lyrics came to him that way and if it ever stopped happening, his career as a songsmith was over! The song was recorded back then by Cab Calloway and Bing Crosby who had minor hits with it. The only other cover to garner charting success was Sinatra's peaking at Number 14. Like many songs that become American Songbook standards, it never was a hit for anyone during the rock era but is a song oft recorded on albums by artists who specialize in easy listening or jazz.

Sinatra tidbit - In February, 1995, he made his last concert appearance in Palm Springs at a gala performance for the Dinah Shore LPGA golf tournament. Just as this song was the first one he recorded to kick off his career resurgence in 1953, his opening number of his final live "set" was "I've Got the World on a String". I doubt if it was coincidence!

Answer: New York

The "Theme From New York, New York" was written by composer John Kander and lyricist Fred Ebb. They had worked exclusively together from the early 1960s until Ebb's death in 2004. Unless you are familiar with the genre "musical theatre", these names may not mean much to you but they had their share of substantial hits, most notably "Cabaret"," Chicago" and "Fosse". Liza Minnelli was associated with them during the filming of "Cabaret" in 1972. When Robert De Niro, the producer and male lead of "New York, New York", was looking for someone to create a musical piece to provide a side plot to the movie, Liza recommended Kander and Ebb. Their first effort didn't meet De Niro's approval but after some quick re-writing, they got the nod and an eventual new entry into the Great American Songbook was conceived.

Sinatra heard Minnelli sing it in the movie when it was released in 1977 and liked it. By then, his musical director was Vincent Falcone. Together they worked out a rendition that Sinatra felt comfortable singing for the first time at a charitable benefit in October, 1978. Then, as Falcone would relate, it took about a year for it to be "Sinatrafied" before being deemed suitable for recording on September 19, 1979. It wasn't an enormous hit upon its release, peaking at a modest Number 32 on the Hot 100. But it sure has withstood the test of time.

Up to that point, the song was Minelli's and the New York Yankee baseball team would play her recording after every game. Subsequent to Frank's recording, his would be played after each Yankee win, her's after each loss. She approached Yankee management and sternly asked for things to be reversed. Their response? Forget it... we'll just not play yours! She stood her ground as did the Yanks so Frank's version is indeed played following every game, win or lose. It truly had become Sinatra's song.

Sinatra tidbits - 1. This was the last song he ever performed in public. It was an unplanned and impromptu rendering at his 80th birthday celebration in December 1995 in, of course, New York City. 2. If you're keeping score of bragging rights, this may have been his most memorable tune featuring an American city, but Chicago wins the numbers game 2-1. Those songs toasting "The Windy City" were "Chicago" and "My Kind of Town (Chicago Is)", two classics in their own right but never Billboard hits.

Answer: Witchcraft

"'Cause there's no nicer witch than you" the lyric goes on to say.

This delightful song, in my opinion anyway, was the first creation by the song writing team of Cy Coleman and Carolyn Leigh. They had been working independently at the Brill Building, met each other at the building's lunch room and after conversing, thought that maybe they ought to write something together. This was it. They would have a couple of modest hits thereafter but their working relationship was a tempestuous one and they went their separate ways in the early 1960s.

With Coleman doing the vocal, they recorded a demo of the song. Leigh had an in with Sinatra's management team having written the lyrics for an earlier hit of his, "Young at Heart". That's where the demo wound up amongst a stack of others in Sinatra's producer's office. Prior to a planned recording session, it was expected that Frank would review them to determine which might be suitable material for the disc. He wasn't particularly interested in spending the day doing that and stipulated that he would just hear a couple... maybe. By chance, this is the one that was pulled from the stack. After a couple of listens, the rest of his team was rather blasé about the song's prospects but Sinatra was hooked. He told them he wanted to record it and that they could choose all the others but "Witchcraft" was definitely in the rotation. Then off he went to the golf course or wherever. With Riddle's wonderful orchestration anchoring the piece, it took about three hours to record.

Sinatra tidbits - 1. Most everyone is aware that Sinatra was the "Chairman of the Board" of "the Rat Pack". However, he was not the original "chairman" - Humphrey Bogart was. Sinatra was part of the original group in the 1950s which included, among others, Lauren Bacall, Judy Garland, David Niven, Cary Grant, Katherine Hepburn, Spencer Tracy and Rex Harrison. Upon Bogart's passing in 1957, he specifically named Sinatra as his replacement and the complexion of the membership changed entirely. Replacing the old guard were Dean Martin, Peter Lawford, Sammy Davis Jr. and Joey Bishop with Shirley MacLean, Marilyn Monroe, Juliet Prowse and Angie Dickenson members of the "ladies auxiliary". Subsequent to Sinatra's divorce from Mia Farrow, Sinatra and Bogart's widow, Lauren Bacall, were reputed to be virtually engaged but ultimately they split, both claiming that they took the initiative. Eventually, Sinatra would marry Barbara Marx, Zeppo's ex-spouse, in 1976 and they remained together for 22 years until his death. 2. Those Number One songs were "Learnin' the Blues" in 1955 and "Strangers in the Night" in 1966.

Answer: Night and Day

Porter wrote "Night and Day" for the 1932 Broadway musical "The Gay Divorce" and it was retained for the movie "The Gay Divorcee". Fred Astaire sang the song in both productions and it was a smash hit vaulting to the top of the charts for ten weeks. By virtue of this hit, he became a well-regarded singer, not just a talented hoofer, and would go on to record seven more Number One hits. Sinatra's version in 1942 was his first charting success as a solo performer reaching Number 16 in March of that year. Although he was still lead vocalist for the Tommy Dorsey Orchestra at the time, this solo project was recorded with Alex Stordahl's band and was the start of a successful ten year partnership together when he severed his Dorsey ties.

In retrospect and considering its enormous popularity with the public at the time, it's hard to believe that the song initially had its detractors including Astaire who actually demanded that it be removed from the musical. Porter's publisher didn't like it and neither did the co-producer of the show. His close friend, actor Monty Wooley, suggested he throw it in the garbage half way through his first hearing. Ring Lardner, the famed sports columnist and author, was particularly harsh but at least in a humorous way. This couplet drew particular scorn:

"Under the hide of me
There's an oh such a hungry yearning inside of me"

In his column for The New Yorker he offered these lines as alternatives:

"Under the bark of me
There's an oh such a mob of microbes making a park of me"

And:

"Under the fleece of me
There's an oh such a flaming furneth burneth the grease of me"

Fortunately, Porter dismissed the criticisms and was adamant that the song would remain unaltered. The one ally he had regarding the song's worth was Irving Berlin who upon hearing it was compelled to send a note to say he thought it was the apex of Porter's career to that point.

Sinatra tidbits - 1. Frank's movie debut as a credited actor was in "Reveille With Beverley" starring Ann Miller. In the movie, various musical stars of the day get a chance to perform a song in what could be considered a music video format. This was his number in the movie. 2. In the mid-1930s before joining the Harry James Band, Frank was a singing waiter at a nightclub in New Jersey, The Rustic Cabin. One evening Porter dropped in with his entourage, returning to New York from the Catskills. When Sinatra became aware of his presence, he jumped onto the stage, publicly acknowledged Porter's presence to the other patrons then he and the band went into a rendition of this song. He got as far as "Night and day, you are the one" then totally forgot the rest of the lyric. In lieu, he kept repeating "Night and day, day and night" for the remainder of the number which I'm sure was mercifully truncated. Whenever they met thereafter, Porter loved to remind Sinatra of his faux pas.

Answer: I've Got You Under My Skin

"I've Got You Under My Skin" was written by Porter specifically for the 1936 movie "Born to Dance" where Virginia Bruce languidly croons the song to Jimmy Stewart. One could honestly say that Bruce could sing but she wasn't much of a vocalist, if you get my drift. Recorded versions by Ray Noble and Hal Kemp that year peaked at Number Three and Number Eight on the charts of the day and both featured a Latin motif, perhaps a bolero or beguine. Undoubtedly other recordings were rendered by jazz and easy listening vocalists between then and Sinatra's version in 1956 but seemingly none stood the test of time.

Considered by many critics to be the masterpiece of the Sinatra/Riddle collaborations, it didn't come easy. Sinatra had never really sung it before but he knew what he wanted out of the melody and shared his vision with Riddle who went to work. On the date of the recording session, Riddle was still making last minute adjustments to the musical chart while riding a cab to the studio. In rehearsal prior to Sinatra's arrival, the musicians stood up and applauded Riddle's score after the first take, a rare tribute indeed. Sinatra was a notorious perfectionist but even so, normally he would get the desired results within a take or two, maybe three. If he wasn't getting it, he'd shut it down, call it an off day and try again another time. On this occasion, he knew he was close and so they tried it again and again until they nailed it on take 22! Sinatra often liked to experiment with the songs he sang regularly... change them up a bit. This is one arrangement that he sang the same way every time right to the grave. He wouldn't mess with perfection.

Sinatra tidbit - After Porter's leg was amputated and he became a virtual recluse, Sinatra was one of the few intimates he would invite over for dinner and cocktails. Porter had lived in a suite at Waldorf Towers in New York for 25 years until his death in 1964. Frank must have felt comfortable there since he took over occupancy of the suite and maintained residence there for another quarter of a century.

Answer: Fly Me to the Moon

The Kramden reference refers to Jackie Gleason's character in "The Honeymooners". Whenever his wife Alice would properly chastise him for doing something stupid, he'd say something like "One of these days, Alice - POW, straight to the moon!" Of course, by the end of the episode, she would be proven right and Ralph would be eating humble pie and pleading for forgiveness.

In the early 1950s, a fellow named Al Livingston signed talents like Riddle and Sinatra to the Capitol label and was the creative force in linking the two of them together for all those great songs and albums. By 1961, however, Sinatra had grown frustrated with the company and his relationship with Livingston was festering. So, despite all the success he had had there, he chose to strike out on his own and form his own record label, Reprise. I'm not sure why he didn't induce Riddle to join him and maybe that relationship had grown stale as well but this venture afforded him the opportunity to work with new people and assay new musical directions. In 1964, he worked with Count Basie and Quincy Jones on an album entitled "It Might As Well Be Swing" and one of the featured tracks was "Fly Me to the Moon".

In 1954, an itinerant pianist named Bart Howard wrote a little ditty entitled "In Other Words" for his employer at the time, NYC cabaret performer Mable Mercer. Other chanteuses such as Kaye Ballard and Felicia Saunders picked up on it and they all sang it much the same way, as a slow waltz. But in 1963, the Bossa Nova craze was in full throttle and another pianist/accompanist for the likes of Peggy Lee and Judy Garland named Joe Harnell worked out an arrangement for the song in that genre. By then, the song had been renamed "Fly Me to the Moon" and Harnell's recording was a major hit, peaking at Number 14 on the Hot 100 and earning him a Grammy Award for Best Pop Instrumental Performance. Subsequently, everyone and his dog recorded it but, as usual, Sinatra's stood out. When the Apollo 11 mission to the moon reached its destination, Buzz Aldrin had a portable tape player and a cassette of the popular music of the day. Naturally, the first song played on the moon was this one... Sinatra's version. Meanwhile, the only song Bart Howard wrote of any consequence earned him so much money, he was able to comfortably retire.

Sinatra tidbit - In the 1960s it was Beatlemania. When Frank was the darling of the bobby soxers in the early 1940s, the screaming, the tears and fainting at the mere sight of Sinatra also had a name. It was Swoonatra!

Answer: What Is This Thing Called Love?

Cole Porter composed this song while he was still an ex-pat living in Paris. With more money than they could possibly spend, he and his wife were frequent travelers and one of their more popular destinations was Morocco. Porter claimed that two of his songs were inspired by his visits there; "Night and Day" through a muezzin's call to prayer and "What Is This Thing Called Love?" from a Muslim chant he heard in a Marrakech market. Eventually, it made its way onto the Broadway stage in 1930 in a production called "Wake Up and Dream" and its exoticism was fully exploited with beating African drums and the like. Leo Reisman had a Number Five hit with it in 1930 with a more conventional approach, out-charting several other competing versions. Artie Shaw's pure instrumental recording stalled at Number 15 in 1939 while Tommy Dorsey's take went to Number 13 in 1942. It's interesting to note that Sinatra was the band's boy singer at the time but Dorsey delegated the vocal to Connie Haines. It would be 13 years before Sinatra got his crack at it.

While most recordings of this song in the past were at mid-tempo, Sinatra and Riddle turned it into a slow ballad, the mood and tone almost introspective. Some analysts of Sinatra's recording speculate that the lyrics struck too close to home, that he was personally wondering "what that thing called love really was". He was still smarting from his and Ava Gardner's separation several months earlier and although he was always ever hopeful that reconciliation was in the works, Gardner was adamant that the affair was over. In her words, things were great in 1951 when they got married while he was down and out but as soon as his career turned around in 1953, he was his old arrogant self and impossible to live with.

Sinatra tidbit - When Sinatra left Harry James' band to join Tommy Dorsey's, his addition elevated a very good band to one that was the best in the business. At the beginning, they got along smoothly and Dorsey gave him a few musical tips that helped him grow enormously as a vocalist. Some dealt with phrasing and timing but the most important piece of advice concerned breath control, the ability to hold notes better than his contemporaries. Dorsey had the same talent playing the trombone and advised Sinatra that he owed the gift to his practice of swimming lengths underwater to increase his lung capacity. Sinatra began to follow the same regimen. Eventually though, they both were too strong willed to peacefully co-exist and they grew to despise each other. Sinatra wanted out and Dorsey agreed provided he would sign over 47% of his future singing royalties. Maybe Sinatra was so eager to go solo he didn't understand the implications of this but it was later rumored that Dorsey waived this claim when Sinatra's godfather, mafia underboss Willie Moretti, visited Dorsey and made him "an offer he couldn't refuse". Long after Dorsey's death in 1956, Sinatra acknowledged his disagreements with him but also stated his mentorship was the most significant factor in making him the success he came to be.

Answer: The Lady Is a Tramp

When I first heard this song as a kid eons ago, I had no idea what it meant and it didn't help never to have heard it in its original context within the play. This ignorance persisted until now when my research unlocked its implications and in case others reading this have been in the same boat, here's what Lorenz Hart was proposing with the lyric. It was a parody originally intended to be sung by a woman of elite social stature about another woman perhaps moving up in class, like Audrey Hepburn's character in "My Fair Lady". Essentially, real ladies (the upper class) do all the things this woman wouldn't; hence this woman is not a lady at all but a "tramp".

"She gets too hungry for dinner at eight
She likes the theater and never comes late
She never bothers with people she'd hate
That's why the lady is a tramp

Doesn't like crap games with barons and earls
Won't go to Harlem in ermine and pearls
Won't dish the dirt with the rest of the girls
That's why the lady is a tramp"

That the song was meant for a female vocalist is borne out by studying its discography. When charting versions were first released in 1937, they were all sung by women, most notably Sophie Tucker and then by Edyth Wright fronting Tommy Dorsey's orchestra. There has never been another recording to crack Billboard's charts, pre or post the Hot 100 era, but notable LP versions have been sung by such female luminaries as Ella Fitzgerald, Diana Ross, Della Reese and Lena Horne. Significant male recordings seem to have been limited to Mel Torme, Tony Bennett and Sinatra and, as is usually the case, Sinatra's version, sung with brio, is the one most critically acclaimed. He just had that knack!

When "Babes in Arms" was converted to the screen, two of the three classic songs from the play were removed from the score - this one and "My Funny Valentine". Only "Where or When" survived the cut. As inexplicable as this decision was, the public response was even more baffling. The Broadway production only survived for 289 performances... not bad but not great. The movie release in 1939 was an unqualified success, the fifth top grossing film of the year! In his guide to the movies, Leonard Maltin gives it two and half stars out of four, a so-so rating. Its competition included "Gone With the Wind", "Stagecoach", "Ninotchka", "Mr. Smith Goes to Washington", "The Hunchback of Notre Dame", "Gunga Din", "Goodbye Mr. Chips", "The Women", "Destry Rides Again", and "The Wizard of Oz", all classics! I have to believe that the casting of Mickey Rooney and Judy Garland had virtually everything to do with the movie's success but I wonder if the stage production would have done better if they were cast in it rather than Mitzi Green and Ray Heatherton.

Sinatra tidbit - Sinatra sings this song to Rita Hayworth in "Pal Joey" while appearing to provide his own accompaniment on the piano. In "Around the World in 80 Days", he's shown as a honky tonk pianist in his cameo appearance. On one of his TV specials, I saw him crooning while seemingly plunking the ivories. However, with the possible exception of a ukulele given to him as a child by an uncle, Frank never learned to play a musical instrument.

Answer: It Was a Very Good Year

Sinatra included this song on his 1965 Grammy winning album "September Of My Years". I was tempted to include that title as one of the distracting answers but then thought better of it. It would be an open invitation to take the wrong answer considering the slice of lyric I used mentioned being in the "autumn of my years". The other answers were certainly relevant anyway, all dealing with reminiscences to times past. "Those Were the Days" was a Number Two hit for Mary Hopkin in 1969; Terry Jacks' "Seasons in the Sun" topped the Hot 100 in 1974 while "Yesterday When I Was Young" peaked at Number 19 for Roy Clark in 1969.

"It Was a Very Good Year" was composed by Ervin Drake in 1961, a fellow who had been working in the business for a number of years and best known for his "I Believe", a huge hit for Frankie Laine in 1953. He was visiting a music publisher friend who advised him Bob Shane, the lead singer of The Kingston Trio, was dropping by his office. If he had a folk song to pass on to Shane, he'd be pleased to accommodate. Drake didn't but adjourned to a vacant room and completed this song in ten minutes. The concept of a fine wine cellar being a simile for life had been percolating in his head for some time and this was the impetus that drew it out. Shane indeed used the song as part of the Trio's 1961 album "Goin' Places" in their usual robust, perfunctory folk singing style. Four years later, Sinatra heard the song on the radio as he was driving to Vegas and perceived different qualities in it. Together with his arranger at the time, Gordon Jenkins, they adapted it into the pensive version we're now so familiar with.

Sinatra tidbit - 1966 would be a very good year for Sinatra. He had four Number One hits on Billboard's Adult Contemporary chart starting with this one in February. "Strangers in the Night" topped that chart for seven weeks in June and July while also reaching the apex of the Hot 100 for a week. Then "Summer Wind" and "That's Life" peaked at Number One in October and December respectively. Finally, he made it back-to-back Grammy wins for best album with the LP "A Man and His Music". Not bad at all for a 50 year old during the rock era!

Answer: Young At Heart

The first line of the song goes "Fairy tales can come true, it can happen to you" and it was becoming a reality for songwriter Carolyn Leigh and, to some extent, Sinatra as well. After his meteoric rise to fame ten years earlier, he had several lean years where it looked like his day had passed. The movie "From Here to Eternity" was certainly a career boost and this song finally reintroduced him to the upper echelons of the Billboard charts. It reached Number Two, his highest charting success since 1947 when "Mam'selle" was Number One. If a comeback classifies as fairy tale-ish, it was happening!

For Carolyn Leigh, there was no question that her fairy tale was coming true. She had mostly been working as an advertising copywriter and was writing lyrics on the side hoping for that first hit song to establish herself in the field. Meanwhile, Stan Kenton's music arranger, Johnny Richards, had been working on a tune for several years that he called "Moonbeam". It came into the hands of a publisher who thought it could use a lyric, passed it on to her and she did her job in about three hours. Then the song languished at the publishers for months with nary a nibble. Finally, Nelson Riddle spotted the score and recognized Richard's name, one that he knew through his friendship with Kenton. He convinced Sinatra that it was a good song and together they did a magnificent job in making it a hit. Leigh would go on to write a couple of more significant lyrics for Sinatra, most notably "Witchcraft" and "The Best Is Yet to Come" and also remained active writing for the stage. For Richards, this was his only song writing credit of note, much preferring his music arranging role with Kenton. Sadly for both, neither experienced the joys of being young at heart in dotage. Richards passed away in 1968 of brain cancer at the age of 56 while Leigh suffered a fatal heart attack at the age of 57 in 1983.

Sinatra tidbit - 1. Frank was in the midst of filming a movie with Doris Day and Gig Young when the song was making its splash on the charts. Seizing the moment, the producers quickly changed the movie's title to "Young at Heart" and the song was used during the opening title sequence and for the closing credits. In typical Hollywood fashion, it didn't matter that the song had no relevance to the movie plot whatsoever. That said, it's not a bad movie at all and worth a look when it makes an occasional appearance on TCM.

Answer: Chicago

"Chicago" was probably the oldest song in Sinatra's catalogue of hits, written in 1922 by an interesting chap named Fred Fisher. Born in Cologne, Germany in 1875, he emigrated to the U.S. in 1900, began composing songs in 1904 and opened up his own publishing company in 1907. For the most part, other lyricists provided the words to his music but, as in this case, he did double duty on occasion, especially in the last half of his career. His first hit in 1907 was definitely a product of its day - "If the Man in the Moon Was a Coon"! Apparently, many hits of the day focused on the moon or "coon" so this was a double-barreled salvo. Songs about that new-fangled invention, the aeroplane, were also popular so it came as no surprise that another chart topper of his was "Come Josephine in My Flying Machine". I actually have a copy of that on CD and his Germanic background is quite evident in the melody, an oom-pah-pah motif. He also co-wrote "Dardanella", Number One for Ben Selvin in 1920 for an amazing 13 weeks and "Your Feet's Too Big" a song I erroneously assumed was written by Fats Waller. Alright, maybe most of you have never heard any of those songs but I'd wager everyone has heard "Peg O' My Heart". That was another of his and Ripley's Believe It or Not asserts that he had written more Irish songs than anyone else in history! After enduring severe pain for three years and numerous operations for cancer, he chose to take his own life in 1942.

The Billy Sunday noted in the lyric was a popular pro baseball player in Chicago during the 1880s. Not much of a hitter, his forte was running and he was an adept base stealer. Hearing the call to evangelism, he retired from ball and apprenticed as a preacher in 1891, eventually heading up his own traveling ministry with the help of his wife. From 1900 to about 1920, he was the Billy Graham of that era. It was reported that at the zenith of his career, he was earning $870/DAY whereas the average working stiff was bringing home $830/YEAR. He hob-nobbed with movie stars, industrialists and influential politicians and it is believed that his stance on temperance was instrumental in the passage of the 18th Amendment enforcing prohibition in 1919. As the song notes, it didn't work that well in Chicago thanks to Al Capone and his gang. Sunday's influence declined in the 1920s when his traveling revivals lost patrons who would listen to radio broadcasts for their sermons.

Sinatra tidbit - Entertainer Joe E. Lewis originally used "Chicago" as his theme song shortly after it was published. In 1927, he ran afoul of the owner of the nightclub he was contracted to and "the boys" sliced his tongue and throat with a knife and left him for dead. He miraculously survived and after several years of vocal rehabilitation, learned to speak but he never was able to sing again when he returned to entertaining. The whole story is told in the 1957 movie "The Joker Is Wild" with Sinatra starring as Lewis. Naturally, he sings the song in the movie and it became something of a signature song for him. That is until 1964 when he starred in another movie set in Chicago with his "rat pack" pals, "Robin and the Seven Hoods". In that movie he introduces "My Kind of Town (Chicago Is)" written by two of his favorite writers, Jimmy Van Heusen and Sammy Cahn. Thereafter, he would sing that song exclusively except whenever he performed in Chicago. Then he would perform both.

Incidentally, I visited Chicago once for three days and loved the place!

Answer: One For My Baby (And One More For the Road)

"Set 'em up Joe, I gotta story to tell ya that you oughta know" the song begins and we sit back expecting to hear a sad tale of love lost. We never get it but rather the poignant reflections of a person wallowing in self-pity and gazing at the world through the bottom of a shot glass.

The melody was a Harold Arlen composition with the heartfelt lyrics provided by the estimable Johnny Mercer who, legend has it, wrote it in 1941 on the back of a bar napkin at P.J. Clarke's, a pub in Manhattan. He was having a torrid romance with Judy Garland and was prepared to seek a divorce from his wife Grace when he heard the news that Garland had eloped with music conductor David Rose. That certainly puts things in perspective!

The song was introduced by our old friend Fred Astaire (who had a habit of doing this) in the movie "The Sky's the Limit" in 1943. Astaire later declared that this was the finest song ever written specifically for him. Could it be that Mercer egged him along with a little story given the accounting above? Anyway, its only significant charting release at Number 21 was recorded in 1945 by Lena Horne, of all people, while Tony Bennett's release of 1957 stalled at Number 49.

Sinatra first put it to vinyl in 1947 but it wasn't until he hired pianist Bill Miller in 1951 that his legendary version took shape. Take a minute (or four) to view this, the definitive Sinatra rendition that, although not acknowledged in any way, must have been a performance from his TV series circa 1958. It's just Sinatra and Miller and pay attention to what he does with his cigarette at about the 40 second mark. What a sense of dramatic timing! https://www.youtube.com/watch?v=m121tmJzcAc .

Sinatra tidbits - In 1964, Miller's house was being washed away in a landslide while the family was still in it. His daughter successfully ran back up the hill and he only survived by hanging on to the bumper of a vehicle. His wife's corpse was discovered the following day, Frank identifying the body since Miller was hospitalized. Sinatra covered the funeral expenses and bought a new residence for the Millers. That's the saintly Frank! Four years later, he was filming "The Detective" and wanted his wife Mia Farrow to appear in it with him. She was already filming "Rosemary's Baby" and refused to break her contract with the film's producers. She was served with a divorce petition on the movie set the following day. That was the vindictive Frank!

Answer: Paul Anka

In 1968, Paul Anka and Frank Sinatra were both working the nightclub circuit in Florida. They knew each other through a mutual acquaintance, Don Costa, and in the course of conversation one evening over dinner, Frank admitted he was fed up with the business. He intended to record one more album then pack it up. Now Anka had always wanted to write something for Sinatra and with this pronouncement, he realized that time was running out. While in France earlier that year, he heard a song on the radio, "Comme d'Habitude", about a man struggling to cope with his failing marriage. While the song itself didn't impress him, he saw something appealing in the melody and decided to try and craft a lyric within its framework that would suit Sinatra. "My Way" would be that song.

"My Way" had middling success on the Billboard Hot 100, maintaining a position on the chart for eight weeks and plateauing at Number 27. However, the story was a little bit different in the U.K. Although the chart placement wasn't significantly higher at Number 18, it refused to go away. It would rise up the chart, fall back, then off the chart entirely, and then return for another run. Altogether, it made nine separate charting appearances for a total of an astounding 122 weeks between April 1969 and January 1972!

Sinatra actually didn't like the song all that much from the start and it's hard to say why he did it to begin with. Perhaps as a favor to Anka? Maybe because he really did intend to retire and didn't think that this was the one song that he'd have to sing at every single, solitary performance he would do for the rest of his career? Anyway, as his daughter Tina avers, Frank did not like the tenor of the song, feeling that it was self-aggrandizing, a trait he despised. He no doubt enjoyed the idolatry rendered to him, but pompous braggadocio was not his style.

Sinatra tidbits - 1. One of Frank's favorite quotes was "May you live to be a 100 and may the last voice you hear be mine". 2. Upon his death, he was buried with a few of his favorite things: a bottle of bourbon, a pack of Camel cigarettes, a Zippo lighter and a roll of dimes. When Frank Jr. was kidnapped in 1963, Frank Sr. was obliged to maintain contact with the kidnappers at their behest and they insisted that all negotiations be conducted through pay phones. On a couple of occasions, the process was jeopardized when he was running out of coins. Thereafter, for the rest of his life, he carried a roll of dimes.


Final footnote - this quiz turned out to be much, much longer than I had envisioned. That's the problem when you're dealing with two interesting topics at once - The Great American Songbook and Sinatra. I also want to acknowledge a few of his songs whose inclusion in "The Songbook" might be considered questionable since hardly anyone else ever did them! Nevertheless, they were favorites of mine and they are: "Summer Wind", "Love's Been Good To Me", "Learnin' the Blues", "The Tender Trap", "All the Way" and his first hit with Tommy Dorsey, "I'll Never Smile Again".