Most film fans in the ‘80s got their first glimpse of John Cusack on the big screen as one of Anthony Michael Hall’s buddies who placed a bet that requires that their pal to secure a pair of Molly Ringwald’s panties in the John Hughes teen comedy “Sixteen Candles.” Hey, everyone has to start somewhere. Consider that his sister Joan was reduced to playing “Geek Girl” with an awkward brace around neck.
It was uphill from there as Cusack, with his ironically humorous takes on leading manhood, became one of the more in-demand male stars for the next two decades, working with such top-notch directors as John Sayles, Rob Reiner, Cameron Crowe, Stephen Frears, Spike Jonze, Woody Allen, Terrence Malick and Mike Newell. Somehow, Cusack has been under the radar when it comes to be nominated for major awards as a performer. But he has made considerable contributions to several Oscar-nominated candidates over the years. Plus, what actor wouldn’t be over-joyed to be associated with an iconic cinematic moment like kick-boxing Romeo Lloyd Dobler’s boom-box serenade from “Say Anything …”.
Tour our photo gallery featuring 12 of his greatest films ranked worst to best, including “High Fidelity,” “The Sure Thing,” “Bullets Over Broadway” and “Love & Mercy.”
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12. “PUSHING TIN” (1999)
Image Credit: Joseph Lederer/20th Century Fox/Kobal/Shutterstock Director: Mike Newell. Writers: Glen and Les Charles. Starring: Billy Bob Thornton, Cate Blanchett, Angelina Jolie.
The flight plan of this off-kilter comedy about dueling alpha-male air controllers whose clashing egos get in the way of public safety is a bit wonky, especially when it plunges into a wife-swapping subplot. It is at its best when it sticks to the intense behind-the-scenes world of overseeing New York City’s congested air space. What saves it from a crash landing is the cast. As uptight Nick, Cusack does a fine job of being threatened by Thorton’s laidback motorcyclist Russell. A tattooed Jolie makes a splash just by pushing a supermarket cart piled with liquor bottles while Blanchett nails her Long Island housewife.
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11. “MAPS TO THE STARS” (2014)
Image Credit: Moviestore/Shutterstock Director: David Cronenberg. Writer: Bruce Wagner. Starring: Julianne Moore, Mia Wasikowska, Olivia Williams, Evan Bird.
By definition, Cronenberg’s films are built to get under our skins and this creepy take on the toxic showbiz realm of Beverly Hills is slithery enough to get the job done by balancing satire and despair. Moore attracted the most praise for her faded actress who was abused by her movie star mother and is trapped in an imaginary world. But Cusack acquits himself well enough as an arrogant TV shrink to the stars who unknowingly married his estranged sister (Williams). Their 13-year-old son (Bird) is a Bieber-level pop idol and rehab veteran who seeks both love and limits in his life. Cusack has called the film’s script as “the most savage destruction of Hollywood fame and secrets” that he has ever seen.
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10. “THE BUTLER” (2013)
Image Credit: Snap Stills/Shutterstock Director: Lee Daniels. Writer: Danny Strong. Starring: Forest Whitaker, Oprah Winfrey, Mariah Carey, Jane Fonda, Terrence Howard, Alan Rickman, Liev Schreiber, Robin Williams, James Marsden.
For this epic biopic loosely based on the life of Eugene Allen, an African-American butler (Whitaker) who served in the White House for 34 years, Daniels mostly pulled off the stunt of hiring unlikely actors as famous politicians, including Williams as Dwight D. Eisenhower, Marsden as John F. Kennedy, Schreiber as LBJ and Rickman as Ronald Reagan. Cusack had the honor of playing Richard Nixon as a laugh-worthy pathetic shadow of a leader who is dissolving before the nation’s eyes. By not caring about turning the actors into mimes, the film humanizes these bigger-than-life figures while revealing their foibles.
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9. “EIGHT MEN OUT” (1988)
Image Credit: Orion/Kobal/Shutterstock Director and writer: John Sayles. Starring: Clifton James, Michael Lerner, Christopher Lloyd, Charlie Sheen, David Straithaim, D.B. Sweeney, Michael Rooker.
In 1919, the Chicago White Sox have a stellar collection of baseball players but they get little monetary compensation for their efforts. Gamblers convince star pitcher Eddie Cicotte (Straithaim) to recruit other disgruntled players to throw the game for money instead of winning the World Series. Cusack as shortstop and third baseman Buck Weaver denied being involved with the scam as his efforts on the field showed, but is still banned from the game for having knowledge of the wrong-doings. Sayles loves his ensemble casts and this one is a goodie. Meanwhile, Cusack gets to deliver one memorable speech about his love of the sport that ends, “When the bat meets the ball and you feel that ball just give, you know it’s going to go a long way. Damn, if you don’t feel like you’re going to live forever.”
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8. “GROSSE POINT BLANK” (1997)
Image Credit: Moviestore/Shutterstock Director: George Armitage. Writers: Tom Jankiewicz, D.V. DeVincentis, Steve Pink, Cusack. Starring: Minnie Driver, Alan Arkin, Dan Aykroyd, Joan Cusack.
This dark comedy answers the question what happens when a hitman goes back to his hometown to attend a high school reunion. Surely, the makers of “Barry” might have seen this rather intriguing movie at some point. Cusack’s Martin Q. Blank is fed up with his profession, especially when a fellow assassin wants to create a hitman union. After a botched job, he takes off to his hometown of Grosse Pointe in Michigan on the advice of his therapist (Arkin), whose secretary books him a hit while he is there. He reconnects with his childhood pal (Jeremy Piven) and former sweetheart Debi, now a radio D.J. (Driver). In the meantime, he is almost killed by another hitman – whom he kills in self-defense, but not before Debi witnesses what happens. More complications arise when he learns who his local target is supposed to be. Peter Travers of “Rolling Stone” wrote at the time that the film “flies on Cusack’s seductive malevolence” while calling him a marvel as a conflicted sociopath.
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7. “THE SURE THING” (1985)
Image Credit: Embassy/Kobal/REX/Shutterstock Director: Rob Reiner. Writers: Steven L. Bloom, Roger Birnbaum. Starring: Daphne Zuniga, Viveca Lindfors, Nicollette Sheridan, Anthony Edwards.
A sweetly funny but far from sappy teen romance that starts off as many rom-coms do – with a college student pair who are clearly meant for each other but they don’t know it yet. Cusack’s Walter Gibson – Gib for short — is a nerd and Zuniga’s brainy and pretty control freak Alison thinks she is too good for him. They end up sharing a ride to L.A. in the same car backseat and get kicked out because of their bickering. They resort to hitchhiking to the West Coast, where her rich but stuffy fiancé awaits. As for the bikini-clad female “sure thing” (Sheridan) that Walter’s friend says is there for the taking, nothing really happens other than he realizes that Alison is the one for him. This role proved to be a break-out for a then-18-year-old Cusack, who soon would stack up a bunch of endearing underdog characters.
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6. “BULLETS OVER BROADWAY” (1994)
Image Credit: Brian Hamill/Magnolia/Sweetland/Kobal/REX/Shutterstock Director: Woody Allen. Writers: Douglas McGrath, Allen. Starring: Jim Broadbent, Harvey Fierstein, Chazz Palminteri, Dianne Wiest, Jennifer Tilly, Mary-Louise Parker.
In Prohibition-era New York, Cusack is David Shayne, an idealistic struggling playwright who is forced to cast a mobster’s extremely untalented and shrill moll, Olive (Tilly), in the show in exchange for financing the production. A hood named Cheech (Palminteri), who is supposed to keep an eye on Olive, turns out to be a savant who comes up with ingenious ideas to improve his play. Meanwhile, David is cheating on his girlfriend (Parker) with the show’s alcoholic diva of a leading lady (Wiest, who won a supporting Oscar for her performance – her second after claiming a trophy for Allen’s 1986 hit, “Hannah and Her Sisters”) as she insists to her young paramour whenever he tries to talk to her, “No, no, don’t speak!” Even if Cusack’s David is a sell-out whose art is barely his own, he still is an easy-to-like charmer. The film earned seven Oscar bids total, including original screenplay, director and supporting actor for Palminteri.
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5. “LOVE & MERCY” (2014)
Image Credit: oger Dufresne/River Road/Battle Mountain/Kobal/Shutterstock Director: Bill Pohlad. Writers: Michael Alan Lerner, Oren Moverman. Starring: Paul Dano, Elizabeth Banks, Paul Giamatti.
This unconventional, uplifting but deeply melancholy musical biopic splits the story of Beach Boys co-founder and leader Brian Wilson between two actors. Dano portrays the 20-something musical genius as he struggles with mental illness and a manipulative father while recording the group’s ground-breaking album “Pet Sounds” in 1966. Cusack takes over as the middle-aged and heavily medicated Wilson as he falls for his second wife, Melinda Ledbetter (Banks), and puts the state of mental health in the often abusive hands of psychotherapist Eugene Landy (Giamatti). The film sounds as if it shouldn’t work — especially since Cusack is less believable physically than Dano – but both stars dig in deep into the emotional wave that drove Wilson and perform a tandem miracle with this portrait of a singular artist.
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4. “BEING JOHN MALKOVICH” (1999)
Image Credit: Melissa Moseley/Universal/Kobal/Shutterstock Director: Spike Jonze. Writer: Charlie Kaufman. Starring: Cameron Diaz, Catherine Keener, Orson Bean, Mary Kay Place, John Malkovich.
Yes, this oddball fantasy is about being John Malkovich – but for only for 15 minutes before you are dropped in a ditch near the New Jersey Turnpike. Cusack’s unemployed puppeteer takes a job as a file clerk in a building with very low ceilings. He finds a secret door behind a file cabinet enters a tunnel and crawls into the actor’s mind. He reveals the portal to his job crush Maxine (Keener) who decides to charge others $200 for the experience. Craig ends having sex with Maxine by entering Malkovich’s head. And the plot only becomes ever more bizarre. Cusack told his agent to find him “the most unproduce-able script he could find. And this was it. That Brad Pitt, Sean Penn, Winona Ryder, Andy Dick, Charlie Sheen and he boy-band Hanson play versions of themselves is a testament to the power of “Malkovich.” The film was Oscar-nominated for director, original screenplay and supporting actress for Keener.
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3. “THE GRIFTERS” (1990)
Image Credit: Moviestore/REX/Shutterstock Director: Stephen Frears. Writer: Donald E. Westlake. Starring: Anjelica Huston, Annette Bening, Pat Hingle.
Lilly Dillon is a longtime con artist who works for a mob bookmaker (Hingle). Her mission is to place large cash bets at race tracks to lower the odds of longshots. She decides to visit her son, Roy, a small-time scam artist, in Los Angeles only to find him beaten and bleeding by one of his victims. Not only does she take an instant dislike to his older girlfriend, slinky Myra (Bening), but she misses a race that would have had a big payoff. Her punishment is getting her hand burned by a cigar. Myra relies on her charms to win over her targets. Soon the two women are at odds, with Roy is stuck in the middle as he catches his mother stealing his cash. Lily relies on a decidedly non-maternal way to make a getaway. Cusack chased after the role after reading the Jim Thompson book it was based on and thought Roy was “a wonderfully twisted role to dive into.” He even studied card, dice and sleight-of-hand tricks with real grifters. The movie was Oscar-nominated for picture, adapted screenplay and lead and supporting actress.
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2. “SAY ANYTHING …” (1989)
Image Credit: Gracie/Kobal/Shutterstock Director and writer: Cameron Crowe. Starring: Ione Skye, John Mahoney, Joan Cusack, Lili Taylor, Philip Baker Hall.
If the Peter Gabriel song “In Your Eyes” immediately makes you think of a unconventional underachiever guy in a baggy coat lifting a boom-box and a brainy beauty who gives her love a pen to remember her by, this smart opposites-attract adolescent romance has worked its lingering magic on you. Rather than smart-alecks and sexpots, it features flawed humans trying to strike a connection and do the best they can, given their peculiar circumstances. Crowe is clearly a star student of Billy Wilder school of screenwriting when it comes to matters of the heart. Just the speech that Cusack’s kickboxing devotee Lloyd Dobler gives when Mahoney as the father of his beautiful, brainy girlfriend Diane (Skye) asks what he wants to do in life over dinner is one for the ages: “I don’t want to sell anything, buy anything, or process anything as a career. I don’t want to sell anything bought or processed, or buy anything sold or processed, or process anything sold, bought, or processed, or repair anything sold, bought, or processed. You know, as a career, I don’t want to do that.”
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1. HIGH FIDELITY (2000)
Image Credit: Touchstone/Kobal/REX/Shutterstock Director: Stephen Frears. Writers: D.V. DeVincentis, Steve Pink, Cusack, Scott Rosenberg. Starring: Jack Black, Lisa Bonet, Catherine Zeta-Jones, Joelle Carter, Joan Cusack, Sara Gilbert, Iben Hjeije, Todd Louiso, Lili Taylor, Natasha Gregson Wagner.
Cusack, who helped develop the movie and pen the script based on Nick Hornby’s book, is Rob Gordon, a music geek who runs a Chicago record store that only sells vinyl. He and his two clerks (Jack Black and Todd Louiso) – who he refers to as the “musical moron twins” – like to mock those customers whose tastes insult their elitist knowledge of songs and artists. As a result, they barely make any money. Rob is dumped by his girlfriend Laura (Hjejle) and he decides to look up those women who he had past relationships with to learn why they left him. This is a movie is made by men who aren’t afraid to be one-upped by every female character who appears on the screen . It also gave Jack Black his breakout role. And Bruce Springsteen actually agreed to make a cameo appearance in the film, giving it added cred. As someone who never married, it doesn’t take a degree in psychology to think this character might be the closest to Cusack’s own personality. Consider that he also had a hand in picking the off-beat tracks for the soundtrack, from “You’re Gonna Miss Me” by the 13th Floor Elevators to “Dry the Rain” by the Beta Band and that he had the locale change from London to his Windy City hometown.
