#10 – ‘Love & Mercy’
The Brian Wilson biopic arrived to "good vibrations" and critical acclaim. Taking place in two time periods, it stars Paul Dano as the young musical genius losing his grip on reality while John Cusack plays the middle-aged Beach Boy struggling to gain control of his life again. Dano absolutely embodies the young Wilson both physically and spiritually. Unfortunately, Cusack... doesn't, although it's not his fault. You just keep thinking, "Hey, it's John Cusack playing Brian Wilson." So in this case, we'll give the "love" to Paul Dano and the "mercy" to John Cusack.
#9 – 'Serendipity'
John Cusack has done better rom-coms. So has Kate Beckinsale. "Serendipity" is not that funny. And it's not that romantic since the two main characters spend most of the movie apart. But their early scenes together make up for all that. How they met and how they'll let fate decide if they're meant to be a couple is all presented in one long sequence that will tickle your brain and melt your heart. But really, it's all about that Kate and Cusack chemistry! Is the story believable? No. But just look at those two! Their movie magic alone gets them on this list.
#8 – 'Eight Men Out'
The sign of any good actor is whether he can work well with others. And Cusack certainly hits a home run in "Eight Men Out". Naturally, it comes at No. 8 on our list. Indie master John Sayles wrote and directed this drama about the 1919 Black Sox Scandal in which mobsters coerced members of the Chicago White Sox to lose the World Series. Cusack plays Buck Weaver, one of the few star players who refused to play badly for the big payout. He's the heart of the team and the heart of the movie. And yet he still pays the ultimate price.
#7 – 'The Sure Thing'
The only sure thing about this list is that "The Sure Thing" was going to be on this list. After only three big-screen credits to his name, 16-year-old John Cusack (16?!) was suddenly cast as a leading "man". Directed by Rob Reiner, it's a college-age comedy wrapped up in a road trip as self-involved Cusack and uptight Daphne Zuniga bicker their way across the country before their banter eventually blossoms into a predictably sweet ending. Even when he's prickly and pretentious, this is the movie that secured Cusack as Hollywood's favourite boyfriend.
#6 – 'The Grifters'
John Cusack has already proven that he can work well with others, but how about working with two Oscar gems like Annette Bening and Anjelica Huston? Without cheating or deception, Cusack proves he can hold his own with anyone. "The Grifters" is a film-noir crime story in a contemporary setting. Anjelica plays John's mom, Annette plays his girlfriend, and all three play con-artists—with the two women competing for Cusack's heart and soul. It's destined to end badly and it does. But yet again, Cusack's roguish charm deceives you into rooting for a devious crook.
#5 – 'Grosse Point Blank'
All right, so we've accepted John Cusack as a captivating con artist. How about John Cusack as a disenchanted assassin? Yes, we can accept that, too. In "Grosse Point Blank", Cusack plays a hitman in hiding during his high school reunion. It's completely unbelievable but that's okay. Because whether he plays a hero or an anti-hero, Cusack, along with his comic timing, can elevate any satirical script into a plausible plot. And this time it's Minnie Driver's turn to play the reluctant love interest who falls for John's considerable charm. And so do we.
#4 – 'Bullets Over Broadway'
John Cusack has more ammunition to play with, in our #4 pick, Woody Allen's "Bullets Over Broadway."
By the mid-90s, Allen became more comfortable staying off the screen and giving his loquacious leading roles to other actors; like John Cusack in this screwball comedy where John plays a tightly-wound playwright who battles divas and gangsters while rehearsing his new play. It's Cusack most honoured film boasting seven Academy Award nominations. Now while Dianne Wiest was the only winner from this film on Oscar night, she definitely received a huge assist from Cusack as her fumbling foil.
#3 – 'Being John Malkovich'
They don't make 'em like this anymore. With our No. 3 pick, it's "Being John Malkovich", the three-time Academy Award nominee, written by Charlie Kaufman and directed by Spike Jonze. John Cusack plays a puppeteer who discovers a portal inside the mind of actor John Malkovich, but just for 15 minutes at a time. You had us at "puppeteer". It's wonderfully weird in all the right places. Take your pick why: Jonze, Kaufman, Malkovich playing himself... But it's still another unique role for the other John in this movie, proving he's certainly got good taste for quirky films.
#2 – 'Say Anything...'
Even if you haven't seen "Say Anything...," you've seen the big-screen moment where John Cusack stands outside Ione Skye's house holding a boombox over his head playing Peter Gabriel's "In Your Eyes". If you want to tell a millennial what gen X is all about, show them this movie. Cusack and Skye are perfectly cast in a teenage love story with likable characters that feel very real in a 1989 world. It's also Cameron Crowe's directorial debut. And his pick of a Peter Gabriel song in a pivotal moment of a John Cusack movie was a pretty inspired choice.
#1 – 'High Fidelity'
"High Fidelity" is peak John Cusack and our No. 1 John Cusack film. He plays every woman's worst nightmare: a narcissistic jerk who won't accept responsibility for his own mistakes. And yet... it's John Cusack so you root for him. Few actors at his age could pull that off in the year 2000. Many fans loved the Nick Hornby book upon which it is based. (Like me.) And many fans were horrified that John and his creative partners moved the narrative from London to Chicago. (Like me.) And yet... it's John Cusack so you forgive him for it.