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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