For about two decades, from the mid-80s through the mid-00s,John Cusackwas one of Hollywood’s most sought-after leading men. He anchored comedies, dramas, and action films with equal success. And he had great romantic chemistry with a laundry list of actresses.
Over the past 20 years, the outspoken actor has spent more time on political causes than good movies, appearing in a series of forgettable direct-to-video projects. But in his prime, Cusack effortlessly inhabited a certain brand of wry but relatable protagonist. He had a “ladies want him, guys want to be him” quality that landed him the lead in more than a half dozen romantic comedies. Following is a listof Cusack’s rom-coms, ranked from worst to best.
8America’s Sweethearts (2001)
On paper,America’s Sweetheartslooked like a slam dunk. Co-written by Billy Crystal, the movie stars Cusack, Julia Roberts, Catherine Zeta-Jones, Hank Azaria, Stanley Tucci, Christopher Walken, and Seth Green. Despite all that talent, this is the most disappointing of all Cusack rom-coms.
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Cusack and Zeta-Jones play actors whose off-screen breakup threatens the success of their latest big-screen release. Roberts plays the sister/assistant of Zeta-Jones’ character, charged with keeping the peace through the promo cycle. Naturally, she and Cusack fall for each other. Much of the blame for this one lands at Crystal’s feet. His attempt at a Hollywood satire felt outdated right out of the gate. And even in 2001, it wasn’t a good idea to put Julia Roberts in a fat suit for the flashback scenes. A major misfire.
7Must Love Dogs (2005)
Cusack plays second fiddle to the great Diane Lane in this movie about a divorced woman dipping her toe back into the dating pool. Cusack’s character, also divorced, must compete for her affectionwith Dermot Mulroneyin one of his signature hot dad roles.
While it’s refreshing to see a movie about two 40-year-old divorcees,Must Love Dogsis blandly predictable and wastes strong performances by its two leads. Cusack and Lane are well-paired, but the script — based on a 2002 Claire Cook novel — gives them way too little to do. It doesn’t even do the titular dogs any favors.
6Serendipity (2001)
Released just five months after America’s Sweethearts,Serendipitypairs Cusack with the luminous Kate Beckinsale in a tale of true love thwarted by fate. Cusack and Beckinsale meet cute when trying to buy the same pair of gloves then spend the evening falling for each other. Beckinsale’s overly superstitious character believes fate will reunite them if they’re truly meant to be together, so they part ways without exchanging numbers. Cut to several years later, when both of them are engaged to other people but suddenly faced with the prospect that they really are destined to be together.
The movie suffers from its too-cute premise and has to overcome the problem of having its central couple separated for the bulk of the runtime. But Cusack and Beckinsale have strong chemistry and some of the screenplay’s tricks are cleverly executed.
Better Off Deadis one of two films Cusack made with oddball writer-director Savage Steve Holland (the second was the following year’sOne Crazy Summer). This one features Cusack as a high school student contemplating suicide after being dumped by his girlfriend.
Poorly received at the time, including by Cusack himself, the filmhas achieved cult statusover the years. Fans will instantly recognize such quotes as “Two dollars!,” “Gee, I’m really sorry your mom blew up, Ricky,” and “That’s a real shame when folks be throwing away a perfectly good white boy.” In addition to the zany laughs,Better Off Deadfeatures a touching central romance between Cusack’s character and a French foreign exchange student.
4Grosse Pointe Blank (1997)
It might be a stretch to call this fan favorite a rom-com — when’s the last time you saw a romantic comedy about a hitman? But Cusack retains his trademark charm even when playing a psychopath, and his chemistry with co-star Minnie Driver has you rooting for them despite yourself.
Co-written by Cusack and directed by George Armitage (whose 1990 filmMiami Bluesis an underrated classic),Grosse Pointe Blanktoes the line between cartoon violence and lighthearted seduction, sometimes in the same sequence. It’s a perfect vehicle for Cusack, who has always been good at thinly masking the darkness behind his characters’ eyes.
3High Fidelity (2000)
Cusack again has a co-writing credit, this time adapting Nick Hornby’s wonderful novel and shifting the action from London to Chicago. Cusack plays a record shop owner obsessed with pop culture and seriously allergic to commitment. He is dumped by his girlfriend (played by Danish actress Iben Hjejle) and spends the movie navigating his emotional headspace in the hopes of being worthy of her again. This is essentiallya coming-of-age movieabout a man in his mid-30s.
High Fidelity, like its source material, is very smart about both music and relationships. It’s smart, funny, and bittersweet. It also features a scene-stealing Jack Black in a role that feels like a spiritual predecessor of his School of Rock character.
2The Sure Thing (1985)
This Rob Reiner comedy— his follow-up to 1984’sThis is Spinal Tap— might seem like it’s in the mold ofPorky’sand other dumb ’80s sex comedies. But the road trip romance has a ton of heart, great laughs, and an excellent central couple, making it one of the best teen rom-coms of the era.
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Cusack plays a wannabe lothario, newly graduated from high school and on the hunt for his next conquest. His best friend sets him up with a beautiful “sure thing” waiting for him in California. He shares a ride with a buttoned-up classmate, played by Daphne Zuniga, and their opposite personalities lead to instant conflict. Their cross-country trek hits one obstacle after another, and of course, they fall in love along the way.
Sadly,The Sure Thing, featuring Cusack in his first starring role, is not available on Blu-ray or streaming.
1Say Anything… (1989)
Writer-director Cameron Crowe’s directorial debutis not just Cusack’s best romantic comedy but one of the greatest of all time.Say Anything…is a hilarious but often poignant look at young love at its most raw.
Cusack plays a high school slacker who seeks to date the smartest, most beautiful girl in school and ends up winning her heart through his sweetness, humor, and undying devotion. The movie avoids the contrived obstacles typical of the genre in favor of genuine emotional turbulence. Ione Skye is luminescent as a young woman falling in love for the first time while also dealing with family trauma in the form of her father’s legal troubles.
As noted throughout this list, Cusack has terrific chemistry with all of his co-stars, but the rapport between him and Skye is off the charts. Their connection culminates in the classic image of Cusack holding a boombox over his head playing Peter Gabriel’sIn Your Eyes. A little stalkerish viewed through a modern lens? Maybe. But a grand romantic gesture nonetheless.
