The best part of comic books as a kid was when one character would meet another. Before it got overdone, it was unexpected and a lot of fun. Movies can be the same way. The criteria for these films was that the crossovers had to take you by surprise and not just be a character from one film graduating to their own sequel, such as Evan Baxter graduating to the lead between Bruce Almighty and Even Almighty or Tommy Lee Jones’ Samuel Gerard character getting his own U.S. Marshalls spin-off. Also, if we listed all the crossovers in Pixar films or Ready Player One, it would just get overwhelming. This criteria belongs to no one but us. Don’t like it? Cool — make your own list!
1. Jay and Silent Bob from Clerks showing up in Scream 3: Your favorite — or maybe not — New Jersey stoners show up to watch the filming of Stab 3 in Scream 3. Yes, things were getting pretty meta in the year 2000.
2. Mortimer and Randolph Duke from Trading Places showing up in Coming to America: Ralph Bellamy and Don Ameche’s rich villains may have lost everything — including that $1 they bet — in the first film, but when Prince Akeem gets them back on their feet with an incredibly generous gift.
3. Billy Cutshaw from The Exorcist being a patient in the insane asylum castle in The Ninth Configuration/Twinkle, Twinkle “Killer” Kane: I know that I said above that character spin-offs aren’t going to be on this list, but this one comes from a movie everyone knows and ends up with one that hardly anybody knows. After being told that “You’re gonna die up there,” by Regan in the first film, this astronaut loses his mind in the second. He’s played by Dick Callinan in former and Scott Wilson in the latter.
4. Paul and Mary Bland from Eating Raoul show up in Chopping Mall: Paul Bartel and Mary Woronov are big favorites here, so when they unexpectedly show up and nearly derail this movie about killer security robots, it’s enough to make me want to stand on my couch and cheer. Actually, that’s exactly what I did. This one also features a cameo from Dick Miller replaying his Walter Paisley character from A Bucket of Blood.
5. Lots of people in She’s Having a Baby: During the end credits, as different real people discuss having a child, Ferris Bueller, characters from TV’s Cheers and Roman Craig and Chet Ripley (Dan Aykroyd and John Candy) from The Great Outdoors all show up in character, connecting all of their various films into one shared timeline (and this movie to the giant wormhole that is the Tommy Westphall Universe).
6. T1000 from Terminator 2: Judgement Day in Wayne’s World: Yep. The knife handed shapeshifting evil cop from Skynet shows up to menace Wayne Campbell and Garth Algar. T1000 also shows up again in Arnold’s Last Action Hero.
7. Michael Keaton playing FBI Agent Ray Nicolette in both Out of Sight and Quentin Tarantino’s Jackie Brown: First, Tarantino asked Keaton to play an FBI agent. Then, when he was asked by Steven Soderbergh to play another FBI agent, Keaton agreed — but only if he could play the same character!
8. Captain Benjamin Willard from Apocalypse Now in Hot Shots! Part Deux: This is about as meta as it gets. Captain Willard is played by Martin Sheen, whose son Charlie Sheen is playing Topper Harley, going through a similar character moment as he enters the “heart of darkness.” The characters’ boats pass one another and they point to each other and mention how much they loved one another in Wall Street, obliterating your reality.
9. Ray Stantz from Ghostbusters shows up in Casper: Sure, he may have a mustache now, but that’s definitely Ray, even if he can’t deal with the Friendly Ghost’s mischief-making. There was also a scene filmed with Zelda Rubenstein reprising her role from Poltergeist which was cut, but hey — Father Guido Sarducci from Saturday Night Live shows up to perform an exorcism and Dr. Harvey turns into the Cryptkeeper from the Tales from the Crypt TV series!
10. Freddy Krueger shows up in the surprise ending of Jason Goes to Hell: At the end of this sequel, Freddy’s claw grabs Jason’s mask, which led to a ten-year wait (!) before these two horror icons finally went claw to machete.
Honorable mentions go to…
Doc Brown from Back to the Future in A Million Ways to Die in the West
Jason Statham’s Frank Martin Transporter character showing up at the beginning of Collateral
Brendan Fraser playing his Encino Man character Link in Paul Shore’s Son In Law and In the Army Now
Gilbert Kane from Alien showing up in Spaceballs
Thanks to Kris Erickson, Jim Sloss, Dan Ayer, Becca and Bill Van Ryn for their help with this list!