Suggestions by @adamatc

Thomas Mann

as Peter Tork in Rockstars Biopics

Thomas Mann

as Peter Tork in The Monkees Biopic

Troy Gentile

as Micky Dolenz in Daydream Believers: The Monkees Story (2012)

Troy Gentile

as Micky Dolenz in The Monkees (2005)

Troy Gentile

as Micky Dolenz in Rockstars Biopics

Troy Gentile

as Micky Dolenz in The Monkees Biopic

Mindy Kaling

as Writer in A 2020-ish What's Up, Doc?

John Turturro

as Judge Maxwell in A 2020-ish What's Up, Doc?

Kimrie Lewis

as Eunice Burns in A 2020-ish What's Up, Doc?

Brad Garrett

as Harry in A 2020-ish What's Up, Doc?

Utkarsh Ambudkar

as Hugh Simon in A 2020-ish What's Up, Doc?

Taika Waititi

as Director in A 2020-ish What's Up, Doc?

Taran Killam

as Frederick Larrabee in A 2020-ish What's Up, Doc?

Leighton Meester

as Eunice Burns in A 2020-ish What's Up, Doc?

Ryan Reynolds

as Howard Bannister in A 2020-ish What's Up, Doc?

Lady Gaga

as Judy Maxwell in A 2020-ish What's Up, Doc?

Michelle Williams

as Clarice Starling in Hannibal

Hal Ashby

as Director in Licorice Pizza (1973)

Cher

as Alana Kane in Licorice Pizza (1973)

William Holden

as Jack Holden in Licorice Pizza (1973)