If Jesus or Tupac ever finally return like we’ve all been saying they will, they should probably do it in a Judd Apatow film or something like that.

We love cameos, don’t we? It’s especially delightful when it’s extremely unexpected, and of course extra points if they are playing themselves – or better yet some kind of silly version of themselves.

It’s all about recognizing the kind of person you are perceived to be, and then playing off that in a way that makes the audience realize that you are in on the joke. If a celebrity is able to do that, it’s instant coolness.

12. Mark Hamill as Mark Hamill in Jay and Silent Bob Strike Back

It takes a very special kind of person to don a spiky wig, giant fist, black cape, and the title Cocknocker. Considering that this film had so many cameos that Kevin Smith actually had to turn people away, it’s very much not surprising to see Mark Hamill turn up in this. In fact it’s almost a mystery why he hadn’t been in a Kevin Smith film before. The cameo couldn’t come at a better time in the film, and the added caption of “Look kids, it’s Mark Hamill!” makes it easily the best appearance in this film.

If you watch the DVD’s behind the scenes features of this film, be sure to check out the stuff about shooting this part. What struck me as especially interesting is watching Kevin Smith talking with and directing Hamill on set – the director is literally glowing the entire time. After all, the man is face to face with his childhood hero, doing something that he never in a million years thought he’d get to do. Not only does he direct Mr. Skywalker in the scene, but he freaking gets to have a light saber fight with him! Not even make-a-wish kids do that!

11. James Taylor as James Taylor in Funny People

Since he appeared in that episode of The Simpsons it’s been clear that James Taylor has a pretty good sense of humor concerning his laid back and folksy persona. But in a film filled with hoards of comedian cameos, the last thing you really expect is this guy. The film does an amazing job of sneaking it up on you – playing Taylor’s “Carolina In My Mind” merely as a background to a brief montage in the film, you expect that to be it. Then once the montage ends we see that the characters have actually found themselves watching Taylor finishing the song on stage.

It’s a great reveal. And if that wasn’t enough, Mr. Taylor gets what is probably one of the best comeback lines in the entire film – which is saying a lot considering the cast. When asked if he gets sick of playing the same songs over and over, he quickly replies to Rogen’s character: “You ever get tired talking about your dick?”

Hearing James Taylor say that filled a place in my heart I didn’t even know was empty. You can’t really ask for more from a film.

10. Kareem Abdul-Jabbar as Kareem Abdul-Jabbar in Airplane!

Years of watching this film, it’s easy to forget just how freaking weird it is to have Kareem Abdul-Jabbar play an airline pilot. Technically he isn’t playing himself, but rather Captain Roger Murdock. However as the above clip shows, he is clearly called out as being an imposter. The scene was probably just meant to comically break the forth wall for a moment, but I always liked to imagine that in the world of the film the actual basketball player Kareem Abdul-Jabbar somehow obtained the identity of an airplane captain and was now attempting to live an alternate life, only to be called out by this young child.

It makes more sense that way, for the best part of this cameo has to be how incredibly out of place he looks sitting there next to Peter Graves. He’s genuinely awkward the entire time – like a man who can’t help but wonder what his agent was thinking when he set up him with the gig.

9. Tom Jones as Tom Jones in Mars Attacks!

Tom Jones always seemed like one of those people who took themselves surprisingly seriously. Mind you I have no evidence of that – it’s just always been a gut feeling of mine… at least until I saw this film. The man clearly knows he’s funny – but not in any kind of debasing way. No one thinks Tom Jones is a fool – no, he’s just so charming ladies man that he’s practically a caricature of himself at this point.

What Mars Attacks does is not lampoon Tom Jones for laughs but rather sticks him in a hilarious situation – in this case, fighting off aliens. It’s just not something you picture the guy doing, and yet once he gets thrown into the mix it becomes oddly natural. So natural that by the end of the film you kind of forget that it’s Tom Jones whipping a ray gun around.

Luckily the movie does a damn good job of reminding you right before the ending credits in what has to be the defining scene of this film. It’s the moment that the story comes to a screeching halt as Jones begins a very special rendition of “It’s Not Unusual” in the middle of a rocky island surrounded by woodland creatures. It’s Tim Burton’s way of pushing this already over-the-top film over its final peak of absurdity.

8. Charlton Heston as Charlton Heston in Wayne’s World 2

Charlton Heston is one of those actors where no matter what you see him in, it feels like he’s too good to be in it. This is why it’s so odd to see him in the sequel to a film based on a damn SNL sketch – it’s just so beneath him… at least it feels that way… honestly after seeing him in that episode of Space Ghost Coast To Coast I have no idea. The man either lost his mind or had a really good sense of humor about himself – either way, good for him.

He’s not even credited in this film as himself, but rather as ‘Good Actor’, which is pretty fitting. It must have been weird to be the other guy, ‘Bad Actor’. That’s like… the worst resume item ever, and judging by his IMDB page (his name is Al Hansen, by the way) he hasn’t really done much more after this film. He’s pretty much immortalized himself as the opposite as Charlton Heston. Meh… better than nothing.

7. Ryan Seacrest as Ryan Seacrest in Knocked Up

This is a rather refreshing cameo. Until this film, Ryan Seacrest pretty much had the personality of a dog – so even if this isn’t his true personality, it’s still nice to see that he can at least pretend to be angry about the bullshit that goes on in the entertainment industry.

To me, this really does seem like the most honest moment of this guy’s career – it’s as if they put him in front of the camera and just told him to say everything he’s always wanted to say. And listening to him rant you absolutely have to agree with him, and you can’t help but to like him and respect him afterward. Say what you want about Seacrest, the man knows good work ethic. He’s not whoring for attention or trying to be something he isn’t – no, he’s just quietly working away, hosting and producing, building up a nice big stack of money.

–~~~~~~~~~~~~–

6. Bruce Willis as Bruce Willis in What Just Happened

If you ask me, this is the best Bruce Willis that Bruce Willis has ever been. Black suit, hot rage, beard. Those are the ingredients for a damn good Bruce Willis. A major plot point of the film, along with the main characters very career, is hinged on convincing this irrational and childish parody of Bruce Willis to simply shave his man beard. It’s perfect because it’s the equivalent of being stuck in the desert with a safe filled with water – you’re so close but you might as well be miles away. The solution is so simple but is guarded by the irrational complexity that is Bruce Willis.

Of course, what makes this especially amazing is that at least according to one director, Willis is a real pain in the ass to work with. It’s not really hard to imagine that to be the case – after all we’re talking about John McClane here – the man has the right to be bossy, or at least thinks he has the right. So if he is the pain in the ass that he’s been rumored to be, that makes this cameo that much more sweeter. Sure he’s a pain in the ass, but he knows it, and knows that it’s kind of funny.

5. Bill Murray as Billy Murray in Coffee And Cigarettes

Bill “Groundhog Day Ghost Bustin’ Ass” Murray. There are so many cameos in this film that it’s hard to pick just one. Every new scene has yet another awesome instance of an actor or musician playing some version of themselves. But what’s terrific about this scene is that you get almost 3 minutes of just GZA and RZA, which is more than enough as the two carry the scene just beautifully on their own – but then, Bill Murray of all freaking people. It’s perfect, a trio made in heaven. What follows is basically what you’d expect, all three men just being awesome.

Then, of course, there’s always this little cameo as himself:

4. Neil Patrick Harris as Neil Patrick Harris in the Harold and Kumar series

Not really a list without this one. The story of how this all came to be is rather awesome, according to an interview with Harris, he had been written into the first film before he had even been asked to appear in the film. That takes some balls to just assume a drug addict sex hound version of Neil Patrick Harris will make it into your film – but hey, they did it. Boy did they do it – the role, which technically isn’t credited as NPH playing himself but rather Neil Patrick Harris playing ‘Neil Patrick Harris’, is one that completely revitalized the man’s career. It’s said that it was this role that got him the gig on How I Met Your Mother.

It was all just too perfect, Harris – an actor known for such an innocent role as Doogie Howser, turned into a such a hilariously demonic alternate of himself. He’s like a caricature of your typical child actor going completely mental. What made it work so well is that they didn’t hold back in the least – every time you thought he couldn’t get crazier he’s suddenly branding a hooker or doing mushrooms.

3. Bob Barker as Bob Barker in Happy Gilmore

Very few things stand up against the test of time in the comedy genre. This is one of those things. Seeing the look on Barker’s face when he springs to life after wrenching Gilmore’s throat is just the scariest and funniest things ever. This is truly one of the best comedic fights – not just because of who is involved but more importantly because of how the fight carries out. Starting with Sandler’s no-warning first swing and all the way to Bob’s final strut of victory as he punches the air in excitement. By far the best move is when Bob lays Sandler out on his back halfway through. And of course, hearing Bob Barker call someone a bitch never gets old.

Of course, Barker only agreed to do this role after being told that he would win the fight. And ever since it’s granted him immense cool points. Just check out this clip from Price Is Right where Barker not only talks about his famed fight, but also gets a cameo of his own.

2. Kurt Vonnegut as Kurt Vonnegut in Back To School

OK – Just what the hell is Kurt Vonnegut doing in a Rodney Dangerfield comedy? Seriously. Don’t get me wrong, it’s totally boss… but… It’s just…

I guess considering that he is only in one shot and probably made a hefty lump of cash for what was at most an hour’s work, you can’t really blame him. Also – it’s actually quite funny. Not so much his appearance, but what follows afterward when his teacher flunks him, saying that whoever wrote the paper “doesn’t know the first thing about Kurt Vonnegut.”

That’s pretty awesome, and it gets even better the following scene where we get to hear Dangerfield cursing out the author over the phone, delivering an F-bomb right back at the man, which of course implies that Vonnegut started the argument, or at least is holding his own during it.

1. John Malkovich as John Malkovich in Being John Malkovich

If you think that writing Neil Patrick Harris into your script is ballsy, how about writing freaking John Malkovich as the pivotal and titular character in your script? Charlie Kaufman, the man behind like… all the weirdest films you’ve seen in the last decade, wrote the film on spec with absolutely no idea if the actor would even consider such an odd role. Luckily he got the script to Spike Jonze. He was able to personally meet with Malkovich at his home and France to try and convince him to play the part which, thankfully for both them and us, he did.

But… can you imagine the awkward conversation that must have led to him saying yes? Malkovich has said that his initial reaction to reading it was that he was “half intrigued and half horrified”, a description that no doubt appears in police reports more than anything else. It really was a dive into the unknown, and it sure did pay off good; not only was the movie a hit but it launched a lot of talented film careers in the process, all while making an entire nation scratch their heads in confusion.

What’s your favorite celebrity appearance?

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