Ever since Marvel’s story-writing algorithm figured out there’s nothing a movie-going audience finds funnier than someone looking at them and saying “Hey, this is all a movie and it’s fake!” Deadpool has enjoyed a career as a leading man. As any true cinephile can tell you, this is well overdue.
Long before Mister Pool was busy saving the MCU, he was saving some of the most storied and celebrated films in cinema history. With both the Oscars and “Deadpool 3” around the corner, we thought now would be a great time to revisit some of Mr. Pool’s pre-mega star work.
Here are the top 30 best picture winners ranked by the strength of their respective cameos from Holywood’s favorite fourth wall-breaking bad boy.
30. The Apartment (1960)
This was one of Deadpool’s first cameos and frankly, he didn’t quite have the formula down. He just randomly bursts into the room and says “I got an apartment for you, it’s called my penis!” and does a little “Hey, look at me, I’m a cool guy” dance.
29. Forrest Gump (1994)
In a way, the character Forrest Gump is sort of the Deadpool of American history the way he just seems to pop up everywhere! That of course doesn’t stop Mister Pool from popping in and doing his thing. Eagle eyes viewers can spot cinema’s favorite 4th wall-breaking mercenary at the Black Panthers meeting, having been hired to assassinate Gump after he inadvertently exposed the Watergate scandal. Deadpool has Gump in his sights, then lowers his gun and says to camera “I can’t kill a mentally challenged guy, what am I, Texas?”
28. One Flew Over the Cuckoo’s Nest (1975)
During one of the more dramatic group therapy scenes towards the end of the film, as McMurphy and Nurse Ratched argue, essentially battling for the souls of the men in the psychiatric ward, the tension is momentarily dissolved when the camera pans over to Deadpool having sex with a chicken and he says “Boy, you guys are seriously nuts!” It’s the only part of the movie Ken Kesey approved of.
27. The Departed (2006)
Colin’s meeting with Costello at his porno theater is interrupted by an irritated patron who tells the two criminals to shut up because he’s trying to watch the movie. They turn toward him, and the camera pans to reveal none other than Deadpool, his feat up on the seats joyfully tossing popcorn into the air and trying to catch it even though he’s wearing a mask. Classic Deadpool move.
26. The Sting (1973)
When Deadpoole pops up to address the audience and confess he would totally go gay for Newman and Redford it kind of takes the sting out of an otherwise iconic high-stakes poker scene.
25. Amadeus (1984)
When Antonio Salieri’s jealousy of Wolfgang Amadeus Mozart reaches a fever pitch he becomes obsessed with destroying him. Still, before he secretly commissions the talented composer to write the requiem that would be his undoing, Deadpool makes his own suggestion. “Just play him this shit!” says Deadpool producing a boom box out of thin air and playing a few seconds of Who Let The Dogs Out.
24. Gladiator (2000)
When you think of this movie, the first scene that likely comes to mind is Russell Crow shouting to the Colosseum crowd “Are you not entertained?!” and then, in a meta twist, having the camera pull out, revealing that the scene is a television set being watched by Deadpool who replies “Meh.” Deadpool proceeds to change the channel to the leg-crossing scene from “Basic Instinct” and says “Here we go!” excitedly retrieving a box of tissues and some hand lotion from beneath his coffee table.
23. The Lord of the Rings: The Return of the King (2003)
As in the first two Lord of the Rings movies, Deadpool frequently pops up begging Frodo for the ring, claiming it’s the only ring that can fit around his hobbit finger-sized cock, which is very funny.
22. American Beauty (1999)
In one of the roles that cemented his career, Kevin Spacey plays Lester Burnham, a sad middle-aged man who becomes infatuated with a high school student. During the iconic rose dream sequence, we hear an off-camera voice shout “Hey, K-Pax!” The camera quickly pans over to Deadpool writhing around in flowers saying “Isn’t she a little old for you buddy?”
21. Rain Man (1988)
When Raymond Babbit accurately counts the number of toothpicks he spills with a single glance, Deadpool jumps into the scene and exclaims “Holy shit, what are you, Rain Man?” This confuses everyone in the scene, and the viewer, because this is the movie Rain Man, and therefore Rain Man is not yet a widely recognized cultural reference. This prompts Deadpool to turn to camera and say “Check please.”
20. 12 Years a Slave (2013)
The merc with the mouth has an abrasive reputation, but he is not completely devoid of tact. He does pop up in “12 Years a Slave” during a brutal whipping scene, but stops himself mid-quip and says “You know what, this is in bad taste, I’m just gonna go, good luck at the Oscars!” He makes a bit of business out of slowly tiptoeing backward out of frame, and for a few beats, we’re distracted by the sounds of glass breaking and cats yelling, each followed by an apology from Mr. Pool, but all in all it’s proof positive that he knows when enough is enough.
19. Lawrence of Arabia (1962)
Deadpool shows up several times during the 3-hour and 38-minute classic film saying things like “Is this shit over yet?!” and “It’s still going? Ugh!”
18. Gone with the Wind (1939)
So many farts.
17. The Godfather Part II (1974)
Michael Corleone’s Senate hearing is an extremely high-stakes scene, but Michael keeps his composure the entire time, dismissing the accusations against him has hearsay and media sensationalism so cooly you the viewer almost believe him. Even when Senator Deadpool presents a teddy bear and insists Corleone point out where on the doll he was touched, Corleone is the epitome of calm.
16. Braveheart (1995)
Few cinematic battlefield speeches are as quotable as William Wallace telling his men “They may take our lives, but they’ll never take our freedom!” It’s an effective rally cry, and the men cheer triumphantly ready for battle, except of course for Deadpool who says “Uhm, what was that first part again?”
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