By Paige Newman
msnbc.com contributor
“Say Anything” (1989)
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20th Century Fox
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When director Cameron Crowe created Lloyd Dobler, he managed not only to write a character most guys think is cool, but he also created every teenage girl’s fantasy boyfriend. And in Cusack, Crowe found someone who embodied the likeable, “who me?” sensibilities of Lloyd, the unassuming but sensitive high school graduate who decides its time to take a shot and pursue his ultra-smart dream girl (Ione Skye). Between Cusack’s speech about what he wants to do with his life, “I don’t want to sell anything bought or processed,” etc. and pondering his break-up with the guys at the Gas and Sip (“Dissed in the Malibu,” says Jeremy Piven in an early performance), Cusack proved you didn’t have to look like Rob Lowe (hey, this was the ’80s) to be the perfect man.
“The Grifters” (1990)
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Miramax Films
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After “Say Anything,” Cusack was definitely looking to break out of those teenage boy roles. What better way than to play the ultimate mama’s boy in this Stephen Frears-directed film noir? The miracle of this film is that it made viewers who had seen Lloyd Dobler just a year earlier put that character on the shelf; here Cusack is cunning, ruthless and desperately caught between his mother Lilly (Angelica Huston), who works for a bookmaker, and femme fatale Myra Langtry (Annette Bening), a con woman with an agenda. He’s a stand-in for the audience in this film and appears as genuinely surprised by all the film’s twists as we are. No matter how dark this film gets, Cusack’s strength is that you want to follow him there.
“Being John Malkovich” (1999)
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USA Films
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Cusack traded his boy-next-door looks for a scruffy beard and unattractive ponytail in this Charlie Kaufman-penned tale in which Cusack’s Craig Schwartz finds a portal into John Malkovich’s head. Anyone who enters, spends 15 minutes in Malkovich’s head (controlling his movements) and then they are spit out into a ditch beside the New Jersey turnpike. Cusack’s normalcy — the way he readily accepts that there’s a 7 ½ floor in the building where he goes for his job — is what keeps the audience involved. At one point Schwartz asserts that the portal belongs to him. “It’s my head, Schwartz, and I’ll see you in court!” Malkovich yells. “And who’s to say I won’t be seeing what you’re seeing ... in court?” Schwartz logically (at least in this surreal world) responds. It’s a role that proved Cusack was ready to take chances. Now, if only he’d take more.
“The Sure Thing” (1985)
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Embassy Pictures
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Though he’d made small appearances in movies like “Class” and “Sixteen Candles,” Cusack really launched his career with this early Rob Reiner film. The character’s own words (describing a kid named Nick) really best describe Walter “Gib” Gibson: “Nick’s the kind of guy you can trust, the kind of guy you can drink a beer with, the kind of guy who doesn’t mind if you puke in his car.” Gib sets his eye on smart girl Alison Bradbury (Daphne Zuniga). He teaches her to shotgun a beer, she moons a driver during their trip across country, and, ignoring her practical instincts, she actually begins to like him. Cusack is a perfect lead, because he never stops seeming like a guy you might have gone to high school with, someone who would have written an English essay about the perfect slice of pizza. As Gib would say, “Bring this man a trough of spritzer.”
“High Fidelity” (2000)
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Touchstone
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Though not without its flaws (one being the horribly sappy ending), this film based on the novel by Nick Hornby gives women insight into the way men think. Cusack’s Rob Gordon is obsessed with three things: music, lists and why he can’t seem to keep a relationship going. He combines all three in his quest to track down the five most memorable breakups he’s ever had. Cusack (who sported his own Fishbone and Clash T-shirts in “Say Anything”) is completely believable as the ultimate music geek who would spout lines such as, “Liking both Marvin Gaye and Art Garfunkel is like supporting both the Israelis and the Palestinians.” Rob is the guy every woman once dated and now looks back on with head-shaking fondness. And for men, he’s relatable, because he’s not some perfect prince charming. The ultimate regular guy, Cusack even makes his flaws work for him.
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