Who is the best painter who never painted for a living?

None of them needed the money and all of them kept going anyway. A few have had museum retrospectives; at least one signed the canvases with a different name.

1

Winston Churchill

Took up oils at 40 and left over 550 canvases; the Wallace Collection is showing more than 50 of them in 2026.

1000pts

2

Ronnie Wood

Trained at art school before the Rolling Stones and never stopped drawing the band.

700pts

3

David Bowie

Painted seriously for decades and collected obsessively; his own work was rarely shown in his lifetime.

700pts

4

King Charles III

A watercolourist for fifty years whose lithographs sell for six-figure sums for charity.

667pts

5

Dwight D. Eisenhower

Started painting in his fifties and produced hundreds of canvases between commands and the presidency.

577pts

6

Sylvester Stallone

Has painted since before Rocky and has had museum retrospectives in Europe.

500pts

7

Lucy Liu

Exhibits under a pseudonym and has shown work in Venice and New York.

500pts

8

Tony Bennett

Signed his canvases Benedetto and got one into the Smithsonian's collection.

409pts

9

Anthony Hopkins

Turned to bold, high-colour canvases late in life and exhibits them internationally.

409pts

10

Frank Sinatra

Painted abstracts in his Palm Springs studio and gave most of them away.

300pts

11

Joni Mitchell

Calls herself a painter derailed by music, and has done most of her own album covers.

300pts

12

Queen Victoria

Kept watercolour sketchbooks for decades and was taught by professional artists.

300pts

13

Jim Carrey

Turned a studio in his house into a full-time painting practice.

167pts

14

Viggo Mortensen

Paints, photographs and publishes his own art books between films.

167pts

15

Miles Davis

Filled sketchbooks in his last decade and used the results as cover art.

167pts