It’s not the weirdest news of 2016, but it’s close: Woody Allen and Miley Cyrus are together at last. The pop goddess will be among the cast in the legendary comic and filmmaker’s forthcoming Amazon series, because who can’t imagine Woody Allen rocking out to “Wrecking Ball”?
And yet Woody’s no stranger to casting well outside his world of old-timey jazz LPs and yammering New York neurotics. Sometimes the unlikeliest people wind up in his movies (and, now, TV show). Here’s a short list of people in Woody Allen films that Woody Allen probably didn’t know existed until a close confidant (say, Soon-Yi) told him about them.
Burt Reynolds, ‘Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask)’ (1972)
’70s cinema belonged to great filmmakers like Martin Scorsese, Steven Spielberg and Francis Ford Coppola. But it also belonged to Burt Reynolds. The actor was becoming one of the biggest stars in the world when Woody cast him in his sketch comedy movie, whose seven segments were inspired by a chapter in David Reuben’s comparatively serious bestseller. Reynolds pops up in the final (and arguably best) one, which plays like a blue version of “Inside Out,” with untold people controlling a man as he bangs his date in a car in a restaurant parking lot. Alas, his part is so small it’s like Woody never even saw “Fuzz.”
Madonna, ‘Shadows and Fog’ (1991)
The cast is so huge in this strange, semi-listless, black-and-white ode to Kafka and existential dread that of course one of Miley’s mentors pops up for a few seconds. During that period when she was actually in movies (and sometimes even good in them), the star plays a carnival tightrope walker who seduces a very serious clown (John Malkovich) away from his waifish ladyfriend (Mia Farrow, natch). The presence of the star of “Dick Tracy” wasn’t enough to attract attention: This is one of Woody’s lowest grossers.
Demi Moore, ‘Deconstructing Harry’ (1997)
Woody Allen movies often seem cast via Mad Libs, and few have felt more random than his star-studded, cuss-heavy account of a Philip Roth-ian novelist (Woody). The movie regularly re-enacts his stories, which means lots of cast members, which means a fair amount of randos — none more rando than Demi Moore. Hot off the scandal that was “Striptease,” she suddenly pops up as a woman who shocks her husband (Stanley Tucci) by fervently embracing Judaism. Anyone could have played her. Why not one of the then-biggest names in the world, long after her best screenwork?
Leonardo DiCaprio, ‘Celebrity’ (1998)
DiCaprio is a serious thespian, so he was bound to wind up in a Woody Allen movie at some point. But the timing was too perfect. Released less than a year after “Titanic,” it gave the then-Tiger Beat hero a small role as a hot-shot, self-destructive movie star who treats our hero (a journo played by a super-stammering Kenneth Branagh) to a crazy night on the town and in his sprawling hotel room. DiCaprio doesn’t even appear to be acting, and no doubt his life hasn’t changed that much since.
Elizabeth Berkeley, ‘The Curse of the Jade Scorpion’ (2001)
We’re in the camp that thinks “Showgirls” knows exactly what it’s doing (please read Adam Nayman's excellent defense book, "It Doesn't Suck"), but for Elizabeth Berkeley, the cost of starring in a “bad cinema” classic is you’re cast into oblivion. And yet Woody took sympathy on her, gifting her with a tiny role in his latest picture. Unfortunately his latest picture turned out to be one of his nadirs. She’s even the target of the single worst ever Woody Allen joke: “She’s got a body that won’t quit.” “Won’t quit? It won’t take five minutes off for a coffee break!” [jumps into a vat of acid]
Tiffani Amber Thiessen, ‘Hollywood Ending’ (2002)
A lot of young actresses have been forced to romance Woody Allen on screen, even when he was past AARP age. Among the more out-there was in this failed farce, in which his temporarily blind film directors is almost seduced by an actress played by the star of “Saved by the Bell” — a show Woody definitely watched a lot.
Andrew Dice Clay, ‘Blue Jasmine’ (2013)
Cate Blanchett won her second Oscar as a troubled woman in this drama, one of the most acclaimed and feted films of his late period career. It also, for some reason, included serious roles for Louis C.K. and, more out there, the guy best known for telling dirty Mother Goose jokes. It was a gamble that weirdly paid off: As a blue collar schmo whose wife ditches him for greener pastures, Clay is both gruff and vulnerable — a tragic figure who will still get in your face. Still, how did he get there? We’d pay a lot of money to watch Woody Allen listening to “Dice Rules.”
BONUS: That time young Sylvester Stallone almost beat up Woody Allen
“Rocky” was five years away, and even prominent roles in the likes of “Lords of Flatbush” and “Death Race 2000” were a few years off. So he wasn’t remotely famous when he popped up in 1971’s “Bananas,” as “Subway Thug.” In fact, he’s one of two oily dudes who almost smack around Woody’s nebbishy New Yorker while he’s riding the MTA. Decades later they’d reunite as buds in the CGI toon “Antz,” but their interactions weren’t as entertaining as they were here.
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