9 Of The Most Entertaining Cameos In Movie History!

What’s more fun than a well-placed cameo? Those brief appearances by a well-known actor or character that has relations to the title their appearing in can really brighten a movie and excite the fans who aren’t expecting them.

In honor of the cameo, I’ve decided to compile a list of cameos that just flat have entertained me over the years. Keep in mind, these aren’t necessarily the best cameos ever done; I know there’s some crazy good ones like the Stooges in It’s a Mad Mad Mad Mad World and so on. No, these are some of the most amusing cameos that brought a little smile to my (and surely many others) face or made people keel over laughing. Some are just classic and some are complete nostalgia, but one thing is for sure… all are a damn good time.

Oh, and I don’t want to hear anything about Neil Patrick Harris from Harold & Kumar. While hilarious, he was playing himself as a full character. You can’t cameo as one of the main parts in TWO movies, even if you are playing yourself.

In some cases there’s a little video included to remind yourself how good these are, so if you enjoy a good cameo like we do, please continue reading to check out 9 of the Most Entertaining Cameos in Movie History!

The Wedding Singer — Billy Idol

An 80’s rock star in your 1998 movie that takes place in the 80’s who’s playing himself? How could that possibly fail? It can’t. The best part about this cameo is that it’s moderately funny when Billy Idol shows up swigging from a bottle on a first class plane ride to Vegas; but when he gets in on the last leg of the movie, it actually becomes a very funny and memorable cameo appearance. I know, this is a really cheesy movie to include, but I happen to like it, so you’ll all just have to bite down. I did place it in the number 9 position. At least I didn’t do like, Adam Sandler‘s cameo in The Hot Chick. Honorable guilty-by-association mention goes to Quentin Tarantino‘s cameo in Little Nicky — a cameo that was supposed to be returned by Sandler in Inglourious Basterds, but that sadly didn’t work out.

Teenage Mutant Ninja Turtles II: The Secret of the Ooze — Vanilla Ice

OK, I know, it’s Vanilla Ice and that’s silly of me to include here. But think back to that time in 1991 when you finally got your second dose of Turtle butt-kicking magic. I was 10 years old and some of the top rapping talents at the time were names like Kris Kross (remember them? They’ll make you jump, jump!) and Mr. Ice, so when he showed up, it was a most entertaining moment. Many years later, I received word that a friend of mine’s buddy was playing in Vanilla Ice’s rock band and they were playing at a bar in Massachusetts. Naturally this was something that could absolutely not be passed up and the night ended with my very own live viewing of “Ninja Rap” being performed. It’s this kind of nostalgia that gives Vanilla Ice the 8-spot.

Scream 3 — Jay & Silent Bob

We all know that Scream 3 was just terrible as a movie, but that doesn’t mean that this cameo isn’t brilliant. As Courteney Cox’s Gail Weathers leaves a movie set, everyone’s favorite stoner pals Jay and Silent Bob walk along while on one of the studio tours. They quickly identify the reporter as Connie Chung and kindly ask how Maury Povich is doing. It’s short, completely random, and incredibly damn funny if you ask me. The only way the movie would have been better is if they ended up being the killers at the end. This cameo was eventually traded for a Wes Craven cameo in Jay and Silent Bob Strike Back. If you haven’t seen Scream 3, then it’s a little tough because you would have to sit through the whole movie to get to this one little itty-bitty part that just might be the only good thing in there, so I’ve included the clip below.

Tropic Thunder — Tom Cruise

In one of the most talked about cameos in recent memory, Tom Cruise appears in Tropic Thunder as Les Grossman, a 100% completely insane studio executive who’s financing the film being made within the film. If you need any proof as to why this cameo is on the list — it may just be the only cameo nominated for a damn Golden Globe. Along with this one cameo, Tropic Thunder itself deserves to be on the list just for it’s massive amounts of celebrity face-peeks.

Hot Fuzz — Peter Jackson, Cate Blanchett

Easily the smallest cameo on our list. In fact, you may not even be aware of these two having been in Hot Fuzz at all. But it’s the hilarious subtly that wins my heart here. Peter Jackson, the man behind The Lord of the Rings trilogy, shows up in a split-second flashback as a drunken mall Santa who stabs Simon Pegg‘s Nicolas Angel in the hand. Cate Blanchett‘s cameo is a little bit more visible… sorta. She plays Angel’s girlfriend-in-disguise as he tries to find her among the identically dressed forensic people at the scene of a crime. Both appear pretty much right at the start of the movie, but I was oblivious to both until months after I had seen it!

Austin Powers in Goldmember — Kevin Spacey, Danny DeVito, Gwyneth Paltrow, Tom Cruise, Steven Spielberg

At current time, Austin Powers isn’t loved quite like it was at the peak of its popularity. Most of its fan base has grown up and the many one-liners were so incredibly over-used that people developed some disdain for the movies — similar to something like Napoleon Dynamite and how un-funny that movie was after its barrage of fan-quoting. But if you go back to when Austin Powers WAS at the peak of its popularity, it’s very hard to beat the reaction that it received for its star-studded opening sequence of Austin Powers in Goldmember. Unfortunately Britney Spears shows up at the end and ruined the mood a bit, but then her head explodes, so everyone wins, folks! Personally, I’d rather see more Austin Powers movies than something like The Love Guru. Re-quench your memory with the clip below!

Anchorman: The Legend of Ron Burgundy — Ben Stiller, Luke Wilson, Tim Robbins

When it comes to the Judd Apatow universe, it’s hard to choose cameos because all of those guys just hang out together on the set of whoever is making a movie at that particular time. Sometimes you wonder if they’re even supposed to be in these movies or if they just showed up and stepped in during a take. But one cameo in particular was just too good to leave off the list. During Anchorman, a massive battle among rival news teams breaks out behind a building. While the various news teams run to join the fight which already includes Will Ferrell and Vince Vaughn‘s respective teams, we see the likes of Luke Wilson and Tim Robbins show up, as well as Ben Stiller as the head of the Spanish news team. Robbins and Wilson show up again a little later in the movie, but I still consider it a cameo and a high one on my list! Honorable mention to a burrito-hating, dog-punting Jack Black.

Jay and Silent Bob Strike Back — Matt Damon, Ben Affleck, and Gus Van Sant

Some people just can’t stand Kevin Smith movies, and I feel sad for those people. Also, I know that Matt Damon and Ben Affleck has their start as part of Smith’s gang, so their showing up in one of his movies is no big deal. But seriously, I have to look beyond all of that and see this simply as one of the most genius cameos of all time. Affleck and Damon appear on one of the many sets that Jay & Silent Bob are running around, and they’re filming their brand new movie Good Will Hunting 2: Hunting Season. For them to take the highly-praised drama from director Gus Van Sant (who’s sitting nearby in this scene, counting money) and turn it into a parody of itself and Hollywood’s over-need for sequels, it was just too perfect. Not to mention the fact that they even went and got the random extra dude from the original movie to use in the cameo spoof!

The Princess Bride — Billy Crystal, Carol Kane

My number one favorite cameo goes without any question. It’s simple, it’s old school, and it’s undeniably good. The movie is The Princess Bride and it’s one of my favorites of all time; the scene is after our hero Westley (Cary Elwes) is killed. In a last ditch effort to bring him back to life, Fezzik (Andre the Giant) and Inigo Montoya (Mandy Patinkin) bring him to the retired Miracle Max for a miracle remedy. The scene is but a few minutes long, but Crystal is in prime form as the miracle worker who looks like he’s about 254 years old. The banter between him and his taunting wife (Carol Kane) is perfect and many quotes came from this one scene, including one of the great quotes, “Bye, bye, boys!” – “Have fun storming the castle!”