Van Gogh (paint brush, mental institute-esque uniform, bloody ear)
Manhattan Woman Going to Work (business attire, pantyhose, sneakers, heels in tote bag)
Andy Warhol
Jeff Goldblum in The Fly, pre-fly
Jeff Goldblum in The Fly, post-fly
Joey wearing all of Chandler's clothes
Doodie Howser
Michelle Branch
The Ruy Lopez

Poop & Pee
Jack White & Meg White
Bono & The Edge
Ab Fab
David Foster Wallace & Bret Michaels
Simon & Garfunkel
Lola & Manni from Run Lola Run
Chris Gaines & Garth Brooks
Donnie Darko & Frank
Donnie Darko & the guy in the red tracksuit
Charlie Rose & [insert guest here]
Ross & Rachel in the "We were on a break" breakup scene
Ross & Rachel in the "Fine by me" scene
Ross & Rachel in Vegas
Slash & Buckethead
Tony & Carmela
The Queen's Gambit & The King's Gambit
Kath & Kim
Matt & Kim
Legolas & Gimli
Steve Vai & Ralph Macchio in the Crossroads guitar battle scene (courtesy of Justin Arcangel)
Johnny Utah & Bodhi
Johnny Utah & Angelo Pappas
Sexyy Red & Trippie Redd
Alicia Silverstone & Liv Tyler in the Aerosmith Crazy music video
Alicia Silverstone & Liv Tyler in the Aerosmith Cryin' music video
Aerosmith Crazy & Aerosmith Cryin'
Lars & Napster
Charlie & Dennis in the scene where they write Dayman

Laird & Sample aka Jessa-Hannah Bluebell Poem Schlesinger-Sackler

Jersey Shore
Jane's Addiction
Bank robbers in Point Break bank robbery scene
The Cody brothers from Animal Kingdom
The entire cast of Animal Kingdom