Editor’s Note: With Ashe taking a much needed vacation, we turn to the insightful talent of writer Maxwell Yezpitelok for this week’s list. Go read more of his work. But read this first. And then go check that stuff out.

Woody Allen has to have one of the greatest casting directors in show business, if we overlook the fact that for some reason they keep casting short middle-aged Jewish guys opposite women like Julia Roberts, Scarlett Johansson and Charlize Theron.

But seriously, look at all the big name stars that keep showing up in his movies, sometimes for the whole movie and sometimes for just a few seconds. In honor of that genius scene in Midnight in Paris where Adrien Brody completely kills it as Dali (only to never again), here are the greatest actor cameos in Allen’s forty-something films:

10. Christopher Walken in Annie Hall

Yes, Marshall Mcluhan gets all the glory, but this isn’t just one of the most bizarre Woody Allen film cameos ever — it’s one of the weirdest scenes in motion picture history, period. It’s just completely out of place in a film like this: with the exception of the short interlude with Diane Keaton and her parents, this sequence could easily belong to some sort of deranged horror movie (something by David Cronenberg, probably).

Walken’s creepy performance turns what was probably meant to be a quick throwaway joke into something truly disturbing.

9. Sylvester Stallone in Bananas

This is just perfect. Five years before Rocky, a virtually unknown (except for fans of Party at Kitty and Stud’s — do not look it up if you’re at work), Stallone plays a subway mugger in this short silent sequence from Bananas. Like almost everything in Woody’s “early, funny movies,” the scene is completely disconnected to the rest of the plot, meaning that Sly’s character sadly doesn’t show up again. Unless you choose to believe that this is Rocky himself, that is.

8. Regis Philbin in Every Thing You Always Wanted to Know About Sex

The most shocking thing here to anyone who wasn’t alive in the ’60s or ’70s is learning that Regis Philbin existed back then, and served pretty much the same role he does today: good natured, inoffensive television host. That’s what makes this skit so hilarious, especially if you imagine Regis is saying that “Do you molest children?” line while making idle conversation with a guest in Who Wants to Be a Millionaire? or something. Incidentally, Burt Reynolds also appeared in the last segment of this movie, playing a brain cell.

7. Larry David in Radio Days

While we never get a good look at him, it’s impossible to miss Larry David’s voice as the communist neighbor in 1987’s Radio Days (which starred a very young Seth Green). A few years later David would become internationally well known as the voice of George Steinbrenner on Seinfeld (and also for co-creating that show, I guess). David also had a short cameo as the theater owner in Woody’s segment in New York Stories, and much later would star in his film Whatever Works alongside some unruly, youthful hair.

6. Sharon Stone in Stardust Memories

She only appears for a few seconds (about a minute in, and then at the very end), but trust me, you can’t miss her. This was Sharon Stone’s first film role ever, and I wouldn’t be surprised if she got every other part in her career because of it. Basic Instinct may be her most famous film, but she’ll always be “Pretty Girl on Train” to me. Fun fact: Stardust Memories was also the first film role of Brent Spiner, the guy who played Data in Star Trek: The New Generation.

5. Jackie Mason in Sleeper

Jackie Mason is a veteran stand-up comedian best known for being extremely Jewish. He plays a robot here. I’ll admit I’m not the biggest Mason connoisseur in
the world, but this scene is hilarious even if you have no idea who he is. Sleeper also features a cameo by then-President Richard Nixon, but I’m not counting it because it’s unclear if it was voluntary.

4. Tim Roth in Everyone Says I Love You

Knowing the context makes this even weirder: Tim Roth’s character is introduced late in the film as a thuggish ex-convict fresh out of jail. In this scene he starts
coming on to Drew Barrymore’s character (who’s engaged to Edward Norton’s character), and just when it looks like she’s gonna have to take out her rape whistle, he starts singing a sweet love song to her. Reportedly, none of the actors in this film knew it was going to be a musical when they signed up for it, but the experiment actually worked pretty well … unlike that time Woody’s producers infamously edited a musical number by The Lovin’ Spoonful in the middle of his movie What’s Up Tiger Lily? without his permission.

3. Leonardo DiCaprio in Celebrity

This one’s a little long (for a cameo anyway), but it really pays off at the end. It’s almost impossible to find video for this scene in The States, but DiCaprio’s ten minutes on screen is his entire role in Celebrity, which didn’t stop the producers from putting his face in the middle of every poster for the film (go on, Google it). Plus, the main guy from Entourage shows up here as a member of DiCaprio’s entourage, thus creating a space-time paradox that could destroy the whole universe if you think too hard about it.

2. Robin Williams in Deconstructing Harry

So you’ve managed to get one of the most recognizable movie stars in the world to appear in your film, and what do you do? Why, you make sure his face is
completely blurred for the entire duration of his scenes, of course. Williams was only one of many celebrity cameos in Deconstructing Harry, though: there’s also Tobey Maguire (NSFW), Julia-Louis Dreyfus (also NSFW) and probably the greatest part in the film, Billy Crystal playing The Devil and comparing sins with a post-Mia Farrow scandal Woody.

1. Jeff Goldblum in Annie Hall

That’s it. That’s Jeff Goldblum’s entire dialogue in this movie: “I forgot my mantra.” And it’s one of the greatest performances in his career. You may have noticed that Paul Simon also shows up in that clip, but he’s actually a recurring character in the movie, for some reason. Like Deconstructing Harry, Annie Hall is packed with celebrity cameos, but the difference here is that most of these actors weren’t
famous at the time: besides Goldblum and Christopher Walken there are cameos by Sigourney Weaver (for about ten seconds), Shelley Duvall, and John Glover, possibly best known as Lex Luthor’s father in the show Smallville.

“Maxwell Yezpitelok has written horror comics and children’s television in his home country, Chile. He’s currently working on his first screenplay, a psychological drama, and he also writes and edits humor articles for Cracked. You can find out more about him by following him on Twitter.

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