Woody Allen’s back catalogue casts a long shadow across contemporary romantic comedy. His tropes and trademarks are as ingrained into the collective sense memory as mother’s perfume. At the first tremble of a clarinet, mutter about mortality or meander across a Manhattan neighbourhood, we inhale the nostalgia like Bisto kids. And arguably we’d never have met Harry and Sally, walked the Sidewalks of New York or dined alongside Friends with Money without his influence.

The Longest Week is peppered with Woody base notes. Over the course of seven days, Conrad (Jason Bateman) has been stripped of the safety net of his wealth and the cushion of his ego, moved in with his cynical best friend (Billy Crudup) and accidentally fallen in love with his girl (Olivia Wilde). His eventual dilemma – to be or not to be a better man – is as timeless as Annie Hall.

Now, to coincide with its DVD release, we look at six other alternative rom coms which wear their Allen affinity with equal pride.

Kissing Jessica Stein (2001)

Kissing Jessica SteinCo-stars Jennifer Westfeldt and Heather Juergensen adapted their 1997 play Lipschtick into this endearingly Allen-esque story of love, Judaism, anxiety and self discovery. Jessica (Westfeldt), despairing at her hopeless romantic life – and under not inconsiderable pressure from her mother to marry – looks for love among the lonely hearts ads. Then finds it in a most unexpected form: Helen (Juergensen).

What follows is the two womens’ attempt to make sense of, and a life from, the tangle of emotions their relationship provokes in everyone it touches. To find a way for Jessica to overcome her fear of *whisper* intimacy. And get a sex life.

Dedication (2007)


Henry Roth (Billy Crudup) is a misanthropic children’s book writer. Mourning the loss of his longtime collaborator from beneath the tower of books he piles on his chest in times of panic. Forced to take on a new illustrator (Mandy Moore) – and confront a level of casual intimacy which makes his OCD flare into mania – Henry’s reluctant evolution is a genuine delight. The directorial debut of Justin Theroux takes a generic girl-fixes-boy story and makes it sparkle with bitterness and biting humour.

David Bromberg’s intelligent characterisations, Tom Wilkinson’s ghostly agony uncle and a stellar supporting cast (Dianne Wiest, Bob Balaban, Peter Bogdanovich and Martin Freeman) all contribute to the magic but it is Crudup’s impeccably delivered cruelty which resonates. Henry’s breathtakingly frank kitchen monologue is textbook Woody Allen. He recounts every significant quirk, fear and fantasy to his speechless new illustrator. Before showing her a Japanese monster movie. And he still gets the girl. Eventually.

Love & Sex (2000)

Love and Sex

Pairing Famke Janssen and Jon Favreau before either embarked on comic book capers, Love & Sex is an underrated meditation on the breakdown of a long term relationship. And a brilliant comedy to boot.

Writer/director Valerie Breiman shares Woody Allen’s ability to harvest her own experiences for rich source material. The result is an autobiographical story heavy with self-deprecation which walks a razor sharp line between loss and laughter. The banter between Kate (Janssen) and Adam (Favreau) is the undeniable star here and the actors’ chemistry undeniable.

If Lucy Fell (1996)

If Lucy FellIn true Allen style, Eric Schaeffer writes directs and stars in this off-beat tale of unrequited love. As with Dedication, If Lucy Fell has a lead oppressed by his own existential dread. And a best friend equally afflicted. Therapist Lucy (Sarah Jessica Parker) and Joe (Schaeffer) counteract their fears – and the dreaded approach of their 30th birthdays – with a pact. Find love or die. Jump off the Brooklyn Bridge together to be precise. They seal the pact with a giant calendar, by way of a death clock, and set out in search of life saving lovers.

The story is undeniably daft. But some of Allen’s best work has more than a touch of the absurd. If you can cast aside cynicism and plunge in you will be amply rewarded. If Lucy Fell is as much a love story for and about a moment in time in New York City as it is the coming together of two lonely hearts. Tongue in cheek commentary on the NY art scene is provided by a dreadlocked Ben Stiller as exuberant artist Bwick – Lucy’s last hope for love – and Joe’s doomed tribute to Jane’s beauty. The end may be predictable but the journey is a treat. And Brooklyn Bridge has rarely looked lovelier.

Trust the Man (2005)

Trust the Man

Tom (David Duchovny) and Tobey (Billy Crudup, again) have let the loves of their lives get away. Which was extremely careless of them. But Tom was preoccupied by a need to have sex as often as humanly possible and Tobey by the awareness of his impending death.

So they have good reason for their neglect. Rebecca (Julianne Moore) and Elaine (Maggie Gyllenhaal) are unsympathetic. And moving on. Rebecca to a new stage production – and a second chance at a career – and Elaine to a brand new relationship with a Teutonic hunk. Through dancing dialogue and a wry insight into the pitfalls of marriage and group therapy, Trust the Man tells an Allen-worthy tale of schmucks and redemption with panache.

Ruby Sparks (2012)

Ruby SparksAlthough 500 Days of Summer is more often cited for its Allen credentials (Joseph Gordon-Levitt, as Tom, does give excellent nebbish man) Ruby Sparks far better epitomises Allen’s ear for the comedic potential of lady-angst.

Real world knowledge and media perceptions reinforce the idea of a sexist auteur preoccupied by self. Yet the actresses who breathe life into his onscreen ‘idols’ speak often of their complexity and veracity. Ruby (Zoe Kazan) is such a creation – imagineered by a bitter and blocked writer (Paul Dano) during a therapy exercise then hauled into three dimensions by the girl who inhabits her. Woody Allen would never have let Summer languish as a MPDG cut out, he would have fleshed her out with thought, word and deed until she stood before Tom as woman not dream.

And Ruby Sparks also remains truer to the powerful Allen tradition of talent crafting characters. Zoe Kazan wrote Calvin and Ruby for herself and partner Paul Dano to portray. She chose her director and took the lead in all significant decisions. Her choices imbue Ruby Sparks with the same command of female voice that Woody’s leads have identified.

Ruby Sparks is not a patronising look at a quirky woman in need of a good man and it is not always a comfortable watch. This is a challenging, often bleak, comedy which shoots straight to the neurosis-riddled heart of a not very good man and defies him to be better. Something Woody Allen would appreciate, one suspects.

The Longest Week

The Longest Week is available on digital download now and on DVD September 1st 2014

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Emily Breen
Emily Breen began writing for HeyUGuys in 2009. She favours pretzels over popcorn and rarely watches trailers as she is working hard to overcome a compulsion to ‘solve’ plots. Her trusty top five films are: Betty Blue, The Red Shoes, The Princess Bride, The Age of Innocence and The Philadelphia Story. She is troubled by people who think Tom Hanks was in The Philadelphia Story and by other human beings existing when she is at the cinema.