By gum...it IS Paul McCartney:
Paul McCartney not only had hits but topped the chart in each of the following guises.
1) Solo - "Pipes Of Peace" (1983)
2) Duo - with Stevie Wonder "Ebony And Ivory" (1982)
3) Trio - Wings ("Wings Mull Of Kintyre" / "Girls' School") (1977) (at this time Wings consisted of Paul McCartney, Linda McCartney and Denny Laine, [guitarist Jimmy McCulloch left the month before to join the re-formed Small Faces])
4) Quartet - Beatles (with John Lennon, George Harrison and Ringo Starr) (16 no. 1s from 1963-1969 in this formation).
5) Quintet - Beatles with Billy Preston - Get Back (1969)
Now, the above is impressive enough. But it gets get better, if a little tenuous;
6) Sextet - Ferry Aid (with Mel Appleby, Kim Appleby, Kate Bush, Boy George, Jim Diamond) (1987)
9) Nine - - with The Christians (Garry & Russell Christian and Henry Priestman), Holly Johnson, Gerry Marsden & Stock Aitken Waterman - "Ferry Cross The Mersey" (1989) - counting Mike Stock, Matt Aitken and Pete Waterman as three separate 'performers' as they had artist credits.
Multi - difficult to know exactly how many performed on this - Band Aid "Do They Know It's Christmas" (with Bananarama, Bob Geldof, Culture Club, David Bowie, Duran Duran, Eurythmics, Frankie Goes to Hollywood, Heaven 17, Human League, Kool and the Gang, Midge Urge, Paul Young, Phil Collins, Spandau Ballet, Status Quo, Sting, The Style Council U2, Wham!). Paul also did a narration for the 'b' side to this disc.
http://www.everyhit.com/record7.html