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Five most Cusackian John Cusack movies -- celebrate the actor tonight

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Join These Things Matter hosts Kevin O'Brien and Taylor Gonda tonight at the Lost Lake Lounge for These Things Matter Night, a live podcast recording dedicated to the films of John Cusack, whose Rob Gordon character in High Fidelity inspired both the title of the podcast and the obsession with pop-cultural minutiae that keeps it going. "Cusack was one of the first things Taylor and I bonded over," says O'Brien. "I've discovered there is a whole legion of man-boys and lady-dudes who, like myself, spent [their] teen years trying to replicate Cusack's angst." To celebrate the career of the actor who continues to inspire them, Gonda and O'Brien have programmed a full evening of Cusack-related entertainment, with screenings and musical performances from SPELLS and Lisa Prank. They'll also be conducting brief interviews with any guest who wants to lionize Cusack for the podcast. Explains O'Brien: "We figured, why not hear from all the other Cusack-philes out there?"

In honor of tonight's event, Westword revisited the filmography of John Cusack and hand-picked his most definitively Cusackian roles. These movies are each thoroughly entertaining on their own merits, but together they illuminate the precise nature of Cusack's appeal. Old-school Cusack fans may notice the conspicuous absence of his broader '80s comedies. Unlike the man himself, Cusack movies like Better Off Dead have aged very poorly. 1985's The Sure Thing is a film that, like promise rings and the music of Rush, is strictly intended to entertain virgins. True fans can hardly begrudge this list, however, as it covers every shade of Cusack, and includes a legitimate masterpiece, two beloved cult classics, a half-forgotten potboiler that deserves a critical reappraisal, and a movie that features what is arguably the best boyfriend of cinema history in its ranks.

See also: Five cult classic horror movies inspired by books -- and available now!

5) Craig Schwartz, Being John Malkovich While Craig Schwartz, a milquetoast puppeteer who discovers a portal into the mind of John Malkovich, stands out as one of Cusack's least likable characters, he embodies the dark side of the actor's sweetly melancholic persona. With his movie-star good looks buried under a scrubby beard and unkempt locks of greasy hair, Schwartz is a chasm of insecurity, a cautionary tale of when yearning curdles into venality. One of the crowning achievements of the metaphysical motherfuckery sub-genre, Being John Malkovich heralded the arrival of screenwriter Charlie Kaufman and filmmaker Spike Jonze, but its conceits are grounded in Cusack's performance. He's the broken, but still-pulsating heart at the center of the story.

4) Rob Gordon, High Fidelity

For many fans, Rob Gordon is the quintessential John Cusack character. Whether its his excellent taste in indie music, romantic escapades with impossibly beautiful women, or his fourth wall-breaking monologues, Gordon connects with proto-hipsters in a way that few other cinematic characters ever have. As the number one, all-time purveyor of top-five lists, we'd like to think that Gordon would personally approve of this inventory.

3) Charlie Arglist, The Ice Harvest

The Ice Harvest is an overlooked gem of a movie. A noir-tinged dark comedy, The Ice Harvest tells the story of Charlie Arglist, a mob lawyer who steals $2 million from his boss. As cinematic heists tend to do, it quickly goes terribly awry, getting bleaker and more hilarious as the film unreels. Cusack deepens a character that could have come across as a stock noir protagonist in the hands of a lesser actor. The film, which is set during the Christmas season, is also perfect holiday movie counter-programming.

2) Martin Blank, Grosse Pointe Blank John Cusack's presence in frothy romantic comedies like America's Sweethearts and Must Love Dogs make him seem unfit for the role of a contract killer on the run. In any other movie than Grosse Pointe Blank, that might be true. As Martin Blank, a moody hitman who returns home for his ten-year high school reunion, Cusack silently conveys how the moral struggle to reclaim the life he left behind is weighted by regret. His chemistry with Minnie Driver makes an implausible romantic subplot ring true, creating one of the most consistently entertaining movies of the Cusack oeuvre.

1) Lloyd Dobbler, Say Anything Easily John Cusack's most iconic role, Lloyd Dobbler from Cameron Crowe's 1988 romantic comedy Say Anything is one of very few dudes who could show up on his ex-girlfriend's lawn blasting Peter Gabriel from a boombox hoisted over his head without being justifiably tasered. Of all the notes struck by a typical John Cusack performance, romantic longing is perhaps the most convincing. He's never better than in Say Anything, a swooning high school romance that honors the intensity of young love. Arguably the best boyfriend of cinema, certainly the least cretinous protagonist of the '80s, Dobbler created a new sensitive-dude paradigm and blazed a trail for moony weirdos pursuing women way out of their league.

Follow Byron Graham on twitter @ByronFG for more mildly amusing sequences of words.

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