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Celebrating The Comedic John Cusack: A Spotlight On His Funniest Roles

November 13th, 2009 10:54am EST | Evan Crean By: Evan Crean
John CusackEven though he doesn't make Academy Award winning material, John Cusack certainly knows how to make entertaining films. Since the early 80s, Cusack's awkward boyish charm has been attracting audiences to his comedies.

While some of his movies over the years have been outlandish and goofy from a plot perspective, Cusack's deadpan sense of humor tends to keep them grounded in a way a lot of viewers can relate to.

Cusack's latest role in Roland Emmerich's "2012" veers away from his traditional light hearted fare toward something heavier. Judging from the previews, it looks like a thriller driven by fancy visuals, yet fraught by overacting and a flimsy plot.

Skeptical of the strength of "2012" as a film, I thought it would be fun to revisit some personal favorite John Cusack comedic roles. If you love John Cusack and you haven't seen these movies, go out and rent them.



Lane Meyer's two loves in life are skiing and his girlfriend Beth. When he fails to make the high school ski team and his girlfriend dumps him for the team's snooty captain, he's devastated. Having lost the most important things in his life, Lane contemplates suicide.

You're probably reading this thinking that nothing about this movie could possibly be funny. "Better off Dead" pokes fun at the idea of a heartbroken teenager even considering the idea, because it teaches there's a whole world out there to experience and no one person is worth obsessing that much over.

The oddball characters are part of what makes this such a funny story. Lane's family is so strange: his delightfully oblivious mother cooks strange concoctions, his father tries desperately to relate to him, and his precocious brother hatches a number of mad schemes.


Cusack's Lane is incredibly silly; he's a shy dreamer, who loses himself in imaginary adventures while trying to handle the typical stresses of adolescence. Curtis Armstrong plays off Cusack well as his burn out friend, providing Lane comical advice about women.



At the time of their high school graduation, many students are poised to pursue a new chapter in their lives. Hoops McCann's hopes of a basketball scholarship are dashed due to a lack of basketball abilities, and the aspiring cartoonist finds himself in need of a stellar portfolio to get into art school.

In an attempt to lift Hoops' spirits, his friend George invites him along to visit family on the island of Nantucket for the summer. On the way, the two run into the rebellious young singer Cassandra, whose grandfather's property on the island is the target of a wealthy land hungry developer (Mark Metcalf). Demi Moore brings a spunky, bad-girl energy to the role of Cassandra which makes her fascinating to Hoops and a perfect foil to Metcalf's unhinged rich snob.

McCann is the most normal character of the lot, a kind-hearted individual with noble intentions to help Cassandra and a natural inclination towards leadership. He is a hilariously sharp contrast to the rag tag group he leads: the overwhelmingly average George (Joel Murray), the cowardly Ack-Ack (Curtis Armstrong) and the dim-witted Stork brothers (Tom Villard and Bobcat Goldthwait).


Together the friends use their unique flair to achieve revenge against the popular kids who spurn them, and help Cassandra triumph over the rich family trying to sabotage her. Along the way Hoops finds romance, as well as the inspiration for his art portfolio.



I promise this is the last movie on the list featuring John Cusack as a high schooler. This is arguably Cusack's most celebrated role. Even if you haven't seen the film you're probably at least familiar with the image of him holding a boombox over his head in a romantic gesture to win his woman back.

The hopeful kickboxer Lloyd Dobler decides to act on his longstanding crush on the valedictorian Diane Court after graduation. What could come off as a creepy advance plays out very innocently due to Cusack's soft portrayal of the character. The overachieving Diane Court appears unsure at first how to handle Lloyd's intentions, but she gradually falls for his charm and his genuine affection towards her.


Diane's overbearing father attempts to come between them because he views Lloyd as a bad influence on his daughter's career aspirations, and for a time he is successful. Love conquers all though, when Diane decides that she won't let her father's disapproval stop her from being happy with Lloyd.



If you ditched your date on prom night and grew up to be a hitman how would you explain it when you returned for your 10 year reunion? That's the question this dark comedy seeks to answer.

A suave killer-for-hire who does his job with a quiet professionalism, Martin Blank is beginning to lose his taste for the career. When the opportunity to make amends for a botched job comes up right in his hometown in time for his high school reunion, the coincidence is just too great to pass up an opportunity to reconnect with the life he left behind.

Martin comically struggles to explain to his friend Paul (Jeremy Piven) and his old flame Debi (Minnie Driver) what he's been doing all these years. Much of the humor in the film is generated by the fact that he blatantly tells people what he does for a living but people scoff and shrug it off like a joke.


Haunted by what could have been between him and former love Debi, Martin desperately tries to rekindle their relationship, while at the same time being hunted by a rival assassin (Dan Aykroyd). The result is pure comic gold, featuring a fantastic soundtrack of 80s hits.



Speaking of great soundtracks, this movie also has great tunes to complement its story. My own top list of John Cusack comedies is much like the top lists the main character Rob makes in "High Fidelity."

Miserable and lonely, the record store owner Rob is dumped by his latest girlfriend Laura because he has not changed since they have met. Dealing with the heartbreak, Rob reviews his top five breakups of all time by flashback in an attempt to figure out where he went wrong, and attempt to win Laura back.

A much more adult John Cusack plays the tormented Rob with a sense of jaded cynicism that's actually a downer for good part of the film. Cusack's Rob is a man trying to put his life back on track again, in an attempt regain the love of his ex-girlfriend. As a viewer you experience a conflict in rooting for Rob, because on one hand he deserves his situation for the mistakes he has made but at the same time Cusack's charm convinces you, that you still want him to succeed.


The film's not completely a downer however. A lot of its humor stems from Rob's interactions with the employees at his record store played by Jack Black and Todd Louiso. Despite working in a record store together their taste in music is incredibly different, which leads to some entertaining arguments.

Disagree with my opinion about what "2012" will be like? Why do you think it might be good? Are there any other John Cusack movies you enjoy that you feel didn't make the cut? Let me know.

Evan Crean
Story by Starpulse contributing writer Evan Crean, a movie trivia guru and trailer addict with a practically photographic memory of actors and directors. Get a first look at the movies premiering each week, which which ones will be worth your $10, which ones you should wait to rent and which ones aren't worth your time.



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