Woody Allen's 10 Creepiest Movies & Moments

Woody Allen's 10 Creepiest Movies & Moments

Sep 22, 2010

Woody Allen’s pseudo-intellectual shtick might have been interesting four decades ago, but over the years his trademark themes (marital infidelity, obsession with death, therapy and Jewish neurosis) have gotten staler than a decade-old Matzah ball. And even without the unmistakable parallels to Allen’s own personal life, his penchant for pairing older men (that he often plays) with decades-younger women has gone from mildly uncomfortable to downright icky.

Allen’s latest, You Will Meet a Tall Dark Stranger, looks to be a retread of more than a few (if not all) of the writer/director’s trademark obsessions. Josh Brolin is a failed writer who believes the beautiful woman in the window across the street might be his muse, while Anthony Hopkins portrays an older man who whitens his teeth, tans his skin and trades up his wife for a young prostitute. Ummm…

Before Stranger hits screens September 22nd, come with us as we look back at the 10 creepiest movies and moments from the Woody Allen oeuvre.

10. The Movie: Celebrity (1998)
The Creepy: Noted thespian Kenneth Branagh delivers an SNL-like caricature of Allen more irritating than amusing. It’s a casting choice that made little sense, proof that Allen was struggling to let go of his cinematic alter-ego resulting in a film as thin as Lorne Michael’s feature-length skit comedy flicks. You wisely may have stepped behind the camera, Woody, but hiring a mimic doesn’t count.
In Allen’s Defense: The latter half of the ‘90s starts to yield concrete proof the movie-a-year pace is dulling skills and growing the turkey pile.

9. The Movie: Everyone Says I Love You (1996)
The Creepy: As usual, Allen favors himself the hapless romantic, employed with the powers of observational humor and intellectual prowess. But as Allen blows on the hair of Julia Roberts after seducing her mentally with his sage-like abilities, her quick kiss isn’t nearly as charming as it would have been in Allen’s slapstick heyday of the mid-‘70s.
In Allen’s Defense: Okay, this one’s more funny than creepy for the most part, so we can give Allen a pass, especially in the context of this largely successful, quirky little musical.

8. The Movie: Curse of the Jade Scorpion (2001)
The Creepy: By this point, it’s getting downright uncomfortable watching Allen plod through his flicks, especially in this miscast, miswritten, mess of a movie. And hypnotized or not, who wants to see Helen Hunt trying to rip Allen’s clothes off?
In Allen’s Defense: Allen’s early-career screwball comedy efforts Bananas, Love and Death and Everything You Always Wanted to Know About Sex... But Were Afraid to Ask are some of his best work; sadly overshadowed by his latter dramatic efforts. It’s understandable that Allen might want to return to such lighthearted fare. The first time was a charm in 2000’s well-received Small Time Crooks, but Scorpion was dreadful by comparison, prompting even Allen to refer to it as his worst work.

7. The Movie: Hollywood Ending (2002)
The Creepy: Only in a movie written and directed by Woody Allen does a guy like this have Téa Leoni for an ex-wife and Debra Messing as a current girlfriend. File this one under the science fiction section.
In Allen’s Defense: Allen has referred to Jade Scorpion as his worse movie, but I’d argue that this one offers it a run for the money.

6. The Movie: Anything Else (2003)
The Creepy: Truthfully, this one is more sad and uncomfortable than creepy. In an age of endless remakes and Hollywood unoriginality, do we really need to see a filmmaker remaking his own movies? In a fruitless attempt to win back the affection of his shrill lost love Amanda (Christina Ricci), Jerry (Jason Biggs) rents a hotel room and tries to seduce Amanda while she suffers from a near breakdown. Allegedly, the scene is supposed to be funny, but it’s more like nails on a chalkboard.
In Allen’s Defense: Here the writer/director appears to be passing the neurotic torch to the next generation, apparently figuring Biggs’d be a fitting successor. The result is a story that feels forced, in a film that seems derivative and pointless.

5. The Movie: Shadows and Fog (1991), Mighty Aphrodite (1995), Sweet and Lowdown (1999), You Will Meet a Tall Dark Stranger (2010)
The Creepy: As we’ve established, Allen’s tastes and interests are well-documented, and he’s returned to them time and again (and again and again). But over the years the director has also shown more than a passing interest in the oldest profession, having featured ladies of the night in about a half-dozen movies, including most recently Judy Punch as Charmaine, love interest to the decades-older Alfie (Hopkins) in Tall Dark Stranger.
In Allen’s Defense: Let us not ruminate too deeply on Allen’s fondness for streetwalkers.

4. The Movie: Vicky Cristina Barcelona (2008)
The Creepy: Allen’s latest muse, Scarlett Johansson, embarks on a polyamorous relationship with Bardem and Cruz. In terms of justification, the plot twist seems more like a pornographic male fantasy than a credible aspect of the storyline. Add to that the disturbing mental image of AARP member Allen crouched behind the camera, fingers entangled like Mr. Smithers, directing Scarlett Johansson and Penelope Cruz during their notorious darkroom make-out sequence.
In Allen’s Defense: At least the hunky Bardem is in the same league as Cruz and Johansson as opposed to more fictional pairings of Allen’s past intellectuals opposite beauty queens.

3. The Movie: Manhattan (1977)
The Creepy: A 44-year-old Allen groping 17-year-old Mariel Hemingway. Period. Thankfully it never gets too graphic, but seeing Woody paired with the shockingly young Hemingway is not only visually jarring, but also kind of hard to swallow.
In Allen’s Defense: The film is one of Allen’s masterstrokes, good enough to make you forget and forgive the inherent irksomeness of Isaac (Allen) winding up with the child-like Tracy (Hemingway). Hey, at least Allen wasn’t that old yet in 1977.

2. The Movie: Whatever Works (2009)
The Creepy: Allen Frankensteins a slightly younger Larry David with his own neurotic tendencies to create one of the most irritating characters in movie history. In this old man fantasy land, young beautiful girls fall out of the sky and land on your doorstep. And lucky for Allen and David, they go for brains over brawn and are willing to overlook personality quirks like singing “Happy Birthday” every time you wash your hands.
In Allen’s Defense: The script for Works sat in Allen’s desk since the early ‘70s (once intended for Zero Mostel) before he threw a shoot together to head off a proposed actor’s strike; proof that some lost projects are best left lost.

1. The Movie: Husbands and Wives (1992)
The Creepy: An unmistakable case of truth mirroring fiction, Allen’s character strays from wife Mia Farrow for his 20-year-old student, played by Juliette Lewis. Meanwhile, in real life, Allen leaves Farrow for her 21-year-old stepdaughter, Soon-Yi Previn. In the most uncomfortable scene, Allen attends Rain’s (Lewis) 21st birthday party at her parents’ house and steals a kiss when the lights go out. “Hi, Dad, did I mention my new beau is old enough to be your father?”
In Allen’s Defense: Strong reviews plus Oscar noms for script and supporting actress Judy Davis. Sadly, the film’s praise and acceptance would give Allen a defense for continuing to cast himself as the romantic lead for another decade to come.

Is Allen creepy, or are we way off? Oh, just agree with us and tell us what you love and hate about his films below.

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