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  • Rough Cut Staff

Four Generations of Male Fantasies


In 2019’s Long Shot, an out-of-work journalist named Fred Flarsky, played by Seth Rogen, ends up in a relationship with Secretary of State and eventual President of the United States Charlotte Field, played by Charlize Theron. This would surprise us in real life. Very few ambitious and successful politicians are single. One example was New Jersey Senator Cory Booker, and Booker is now dating Rosario Dawson, which is different than dating an out-of-work journalist played by Seth Rogen, I would say.

In movie life, on the other hand, an ambitious, gorgeous woman dating a somewhat slobbish man without a job does not surprise us. Is he funny and charming in a self-aware, self-debasing sort of way? Check. Does he help her mellow out by giving her drugs? Check. Is it her job to help him realize he needs to grow up? Check. These are staples of an entire sub-genre of comedies –often romantic, sometimes raunchy – that has been around for decades, slowly evolving but retaining its core tenets.

The trend follows a similar path: Hollywood identifies its leading man and builds a movie and a cast around him. In the last decade, female-led romantic and raunchy comedies have become more popular, mercifully sparing us the rote rehashing of this trend and instead launching some of the funniest, freshest films in recent years, including Bridesmaids, Girls Trip, To All The Boys I’ve Loved Before, Booksmart, Crazy Rich Asians, and Juno.

But for decades, Hollywood tried to stuff this new kind of romantic leading man down our throats. In honor of Charlize Theron month at Rough Cut Cinema, we’re calling these the Bombshells and Long Shots. Here are our four generations. Hopefully there won’t be a fifth.

The First Generation: Revenge of the Nerds

Mid-70s – Late 80s

Major Players: Woody Allen, John Hughes

United Artists

Do we have Woody Allen to thank for four decades of romantic comedies? Maybe, maybe not. But Woody Allen undoubtedly remade the leading man in his own image. As the writer-director of Annie Hall, he created the neurotic, sarcastic, witty anti-hunk: Alvy Singer. As the movie’s star, he inhabited Singer, lending his particular mix of confidence and self-doubt, hyper self-awareness, and manic energy.

And though he branched out slightly, Allen returned to the basic formula of his breakout romantic comedy time and time again. Over a five-year period, Allen cast himself opposite Diane Keaton (x2), Charlotte Rampling, Marie-Christine Barrault, Jessica Harper, Mariel Hemingway, and Mary Steenburgen.

If Woody Allen occupies one spot on the modern rom-com Mount Rushmore, John Hughes earns the second as the creator of one of its most popular sub-genres: the teenage coming-of-age story. Probably most remembered for The Breakfast Club, one of Hughes’ most lasting legacies is the creation of the modern nerd prototype: half Anthony Michael Hall, half Jon Cryer. Known affectionately as “the brain” in The Breakfast Club, Hughes’ nerd is lovable but anxiety-ridden; reluctant lapdog; and simultaneously too good and never good enough for the leading lady (usually Molly Ringwald).

But Hughes departs from both Allen and his successors in one crucial respect, including in both Pretty in Pink and Sixteen Candles: the nerd doesn’t get the girl in the end. That would change very quickly.

Also Notable: Billy Crystal (When Harry Met Sally)

The Second Generation: The Ambitious Underachievers

Late 80s – Early 2000s

Major Players: Jim Carrey, John Cusack

20th Century Fox

As a new era dawned, the long shots set their sights even higher: if Woody Allen could anchor a dozen romantic comedies, why couldn’t they break-out of the rom-com mold, becoming true leading men of Hollywood? These are the slackers, the screwballs, and the screw-ups whose humor may have helped them get the girl, but who spent a decade trying to be more than just funny men in leading roles; they wanted to be leading men who happened to be funny.

The screw-ups were led by one man: Jim Carrey. The King of the “failed X” sub-sub-genre, Carrey was a true chameleon, able to pull-off a failed television reporter (Bruce Almighty), a failed bank clerk (The Mask), a failed private detective who can’t even pay rent (Ace Ventura: Pet Detective), a failed state trooper (Me, Myself, and Irene), and a failed lawyer and husband (Liar Liar). What the man could never fail at? Landing the girl, of course. Always inspired by the love of a good woman, the unlikeable but funny Carrey starred opposite Jennifer Aniston, Cameron Diaz, Courtney Cox, Renee Zellweger, and Maura Tierney.

While Hollywood mostly abandoned the asshole-screw-up model that Carrey perfected, it would return to the slacker prototype for decades. Just one year before Richard Linklater’s Slacker would take the indie film world by storm, John Cusack originated one of the most popular slacker love interests: Lloyd Dobler. An alumnus of John Hughes movies himself, Cusack is the ultimate loveable underachiever, and the sight of Dobler, trenchcoat draped across his awkward shoulders, radio above his head, is the enduring image from Say Anything.

It’s another scene from the cult 1989 comedy that represents three decades of slackers. Asked what he wants to do with his life by his overachieving girlfriend’s father, Lloyd simply says he wants to “spend as much time possible with Diane…I don’t want to sell anything, buy anything, or process anything as a career…What I’ve been doing lately is kickboxing…I don’t know, I can’t figure it all out tonight, sir, I’m just gonna hang with your daughter.” Notably, Dobler departs from the characters of his inspiration (Hughes), this time ending up with the girl, Ione Sky’s valedictorian.

Cusack would return to the slacker role, whether as an unemployed puppeteer (Being John Malkovich) or an unambitious record store employee Rob Gordon (High Fidelity). Sometimes successful, but always disillusioned (see also his depressed hitman in Grosse Pointe Blank), Cusack’s devil-may-care personality seemingly made him the perfect match for his counterpart strivers, including Minnie Driver and Iben Hjejle. He would inspire two decades of underachievers.

Also Notable: Bill Murray (Groundhog Day, Lost in Translation)

The Third Generation: The Loveable Idiots

Late 90s – Mid 2000s

Major Players: Ben Stiller, Adam Sandler

New Line Cinema

The late 90s were a weird time. There’s no reason why the diminutive son of comedy legends Jerry Stiller and Anne Meara and the goofy SNL-alum and star of both Coneheads and Airheads should have become two of the leading romantic-comedy heart-throbs of the era. Yet for just over half a decade, Ben Stiller and Adam Sandler brought their undeniable knack for physical comedy to the big screen, putting themselves through immense physical and emotional pain to make audiences laugh and their counterparts fall in love.

Perhaps the two conspired on the set of Happy Gilmore, where Sandler’s high-strung golfer becomes a better person with the help of the level-headed, over-competent Virginia Venit (Julie Bowen) – and where Ben Stiller popped up in a cameo. By 1998 these two personalities took the world by storm as idiot-savant romantics, winning the hearts of two of the three future Charlie’s Angels in There’s Something About Mary (Cameron Diaz) and The Wedding Singer (Drew Barrymore).

Sandler would continue as the clueless but cute romantic interest to Winona Ryder in Mr. Deeds, Patricia Arquette in Little Nicky, and Drew Barrymore again in 50 First Dates. He simultaneously invented and perfected the archetype of a leading man who we love because we pity him – something that would surely shock the likes of Humphrey Bogart and Clark Gable.

Stiller, on the other hand, became a master at playing the tightly-wound “straight man” – the bland insurance salesman (Along Came Polly) or nurse (Meet the Parents) who reluctantly abides by the quirkiness of those around him, and eventually loosens up.

Both were polar opposites of the second generation: they were the funny men who just happened to be in romantic leading roles. Neither man would make an entire career out of their lovable idiot love stories, both investing more heavily in their humor than their status as romantic leads. But this phase of their careers would influence the generation to come.

Also Notable: Jimmy Fallon (Fever Pitch), Farrelly Brothers (Fever Pitch, There’s Something About Mary, Shallow Hal)

The Fourth Generation: The Raunch-Com

Mid-2000s – Present

Major Players: Judd Apatow, Seth Rogen, Jay Baruche


Enter Judd Apatow: the bridge from Say Anything’s Lloyd Dobler to Long Shot’s Fred Flarsky. Apatow took the slackers and assholes of the second generation, added the irreverent filth and physical comedy of the third generation and the Farrelly brothers, and threw in a dash of heart to create a new prototype: the raunch-com.

The raunch-com’s hero? An under-achieving nerd trying to get the girl. The era has been defined not by a single star – though Seth Rogen is as good a representative as any – but by a rotating cast of slacker geeks. The era kicked off with Apatow’s film breakout, The 40 Year-Old Virgin, quickly establishing all the basic tenets: A nerd (Andy, played by Steve Carell) who works at an electronics store, loves action figures and video games, and can’t successfully talk to girls; a woman (Catherine Keener) who inspires the man to sell his action figures and outgrow his mental and emotional adolescence; and plenty of gross-out comedy in between.

Apatow repeated the formula two years later with Seth Rogen and Katherine Heigl in Knocked Up. He shifted to a mix of dramatic or straight up comedy (Funny People, Get Him to the Greek), but handed the reins for his raunch-com mold to an entire generation. You’d be excused for thinking Apatow had a hand in loser-gets-the-girl films like Superbad (Jonah Hill and Emma Stone), Forgetting Sarah Marshall (Jason Segel, Kristen Bell, and Mila Kunis), or She’s Out of My League (Jay Baruchel and Alice Eve).

This latest generation quickly morphed into a version of male fantasy wish fulfillment, with movies like Fanboys and I Love You, Beth Cooper speaking directly to the aggrieved “fanboy” crowd. Other movies like Zak and Miri Make a Porno (featuring another Seth Rogen performance, this time opposite Elizabeth Banks) have slightly more artistic depth, though nonetheless follow a similar formula.

Also Notable: Paul Rust (I Love You, Beth Cooper)

Long Shot may be the last in a dying generation – it’s at least somewhat self-aware of its own genre’s failings, and has the decency to culminate in Fred’s position as the “first mister” to his wife, President Charlotte Fields. Is this the ultimate fantasy of the underachieving male who wants to do nothing but still end up with his "perfect girl," or a subversion of the need for men to be seen as the primary earner and power center in a relationship? Either way, it’s the inevitable endpoint of a subgenre that turns slackers into sex symbols, slobs into heartthrobs, and losers into heroes. Good riddance.


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