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John Cusack in 'Say Anything'John Cusack has played an impressive variety of movie roles over the years -- but one genre in which he has consistently excelled is romantic comedies.

Indeed, many women who grew up watching his self-deprecatingly funny, realitically cool, hopelessly romantic characters felt let down when it came to their actual, real-life boyfriends. How could mere mortals compete with the sweet, lovestruck smart-asses that Cusack embodies onscreen? These characters, spouting fantastically witty yet sensitive dialogue made up by screenwriters (including Cusack himself in the case of 'High Fidelity'), are, of course, fictional constructs.

But we won't let reality get in the way of our fantasies. On the occasion of Cusack's 44th birthday (June 28), we're celebrating with a Top 5 list that would make Cusack's Rob in 'High Fidelity' proud: our all-time Top 5 Cusack Character Boyfriends. John Cusack in 'Say Anything'John Cusack has played an impressive variety of movie roles over the years -- but one genre in which he has consistently excelled is romantic comedies.

Indeed, many women who grew up watching his self-deprecatingly funny, realitically cool, hopelessly romantic characters felt let down when it came to their actual, real-life boyfriends. How could mere mortals compete with the sweet, lovestruck smart-asses that Cusack embodies onscreen? These characters, spouting fantastically witty yet sensitive dialogue made up by screenwriters (including Cusack himself in the case of 'High Fidelity'), are, of course, fictional constructs.

But we won't let reality get in the way of our fantasies. On the occasion of Cusack's 44th birthday (June 28), we're celebrating with a Top 5 list that would make Cusack's Rob in 'High Fidelity' proud: our all-time Top 5 Cusack Character Boyfriends.

John Cusack and Diane Franklin in 'Better Off Dead'5. Lane Meyer in 'Better Off Dead' (1985)


Even in this quirky -- at times surreal -- comedy, full of eccentric characters and sight gags (like a claymation hamburger rocking to Van Halen), Cusack is totally boyfriend-worthy. A geeky but endearing high school kid who loses his beloved girlfriend to the school's top ski jock, Lane is also tormented by a psychotic paperboy. He repeatedly tries to kill himself before finally finding love with French exchange student Monique (Diane Franklin).

Why he makes a great boyfriend: Though angst-filled, Lane still manages to be funny and sweet; he rescues Monique from her clueless, insulting host family and brings out her real personality.

Significant quote:
"She only speaks French, Roy. She doesn't speak imbecile."

John Cusack and Daphne Zuniga in 'The Sure Thing'4. Walter "Gib" Gibson in 'The Sure Thing' (1985)

In this Rob Reiner-directed film, Cusack -- in his first major role -- is a careless but charming Ivy League college freshman who repeatedly strikes out with his straightlaced crush, Alison (Daphne Zuniga); so he decides to visit his pal (Anthony Edwards) in California where the promise of sure sex with a hot babe (Nicollette Sheridan) awaits. When Gib and Alison both cop the same disastrous ride out west with a perky driver (Tim Robbins) and his equally cloying girlfriend, true love results.

Why he makes a great boyfriend: Gib is both cool (he wears black Chuck high-tops) and sensitive (he writes self-revealing essays in English class). He's also protective: When he and Alison decide to hitchhike separately, he stows away in the bed of a truck that picks her up and winds up rescuing her from the creepy driver by acting like a lunatic.

Significant quote: "When I get out of jail, I'm 36 years old ... And then one day they find me, face down, talking to the gutter, clutching a bottle of paint thinner. And why? Because you wouldn't help me in English, no! You were too busy to help me! Too busy to help a drowning man!"

John Cusack and Kate Beckinsale in 'Serendipity'3. Jonathan Trager in 'Serendipity' (2001)

This rather lightweight, predictable rom-com is made charming by its leads: Cusack is a cool, witty New Yorker who meets equally appealing Brit Sara (Kate Beckinsale) in Bloomingdale's, where they have a "moment" and then spend an incredibly romantic evening together before parting ways and leaving their future to fate (her idea). Years later, on the eve of their respective weddings, they can't stop thinking about each other and hope that destiny reunites them.

Why he makes a great boyfriend: Jonathan's wildly articulate, and it's obvious he enjoys real, heartfelt conversations -- the way to many female hearts. Also, he lives for romance; it's only when he decides to search out Sara that he comes alive. Plus, he gallantly lets her have the pair of gloves they both had their eye on in Bloomie's.

Significant quote:
"You know, maybe you should give me your phone number. Just in case ... In case of life. I just had a really great time and for all we know I wouldn't be able to find you again.

John Cusack and Iben Hjejle in 'High Fidelity'2. Rob Gordon in 'High Fidelity' (2000)

In Stephen Frears' wonderful adaptation of Nick Hornby's novel, Cusack plays a slacker -- albeit a funny, highly intelligent one -- who owns a vintage record shop in Chicago, staffed by two classic music geeks (Todd Louiso and Jack Black). Rob makes innumerable Top 5 lists, including his Top 5 Breakups; his latest girlfriend, Laura (Iben Hjejle), has just left him because of his inability to commit. He decides to seek out past girlfriends (including Catherine Zeta-Jones) to find out what went wrong, hoping to win Laura back.

Why he makes a great boyfriend: Rob's a decent human being whose employees like him so much they hang out at the shop on their days off; he makes a Top 5 list of things he misses about Laura; he's introspective and motivated enough to figure out where he failed, relationship-wise. Plus he has great taste in music.

Significant quote: "She didn't make me miserable, or anxious, or ill at ease. You know, it sounds boring, but it wasn't. It wasn't spectacular either. It was just good. But really good."

Ione Skye and John Cusack in 'Say Anything'1. Lloyd Dobler in 'Say Anything' (1989)


Not only is Cameron Crowe's funny, intelligent movie one of the best, most honest teen romantic comedies ever, but Cusack's underachieving, eternally optimistic Dobler is the ultimate onscreen boyfriend (and the character that defined Cusack as one of the era's finest young actors). Intense, fast-talking Lloyd has no plans beyond kickboxing championship, so when he falls for fellow graduating senior and class valedictorian Diane (Ione Skye), there are complications, mainly because of her overprotective father (John Mahoney). Lloyd persists, however, in following his heart.

Why he makes a great boyfriend:
He actually admires Diane for her brains (of course she's also very cute); he's completely honest and open about his intentions and life in general; when they break up, he serenades her by holding a boombox playing Peter Gabriel's 'In Your Eyes' outside her bedroom window.

Significant quote: "What I really want to do with my life -- what I want to do for a living -- is I want to be with your daughter. I'm good at it."