From early 80’s classic like “Say Anything…” to modern favorites like “Serendipity,” these five John Cusack chick flick movies showcase Cusack’s unmatched talent as one of today’s most celebrated actors and include some of his best performances as a romantic leading man.

  1. "Say Anything… " Marking a more serious turning point in John Cusack’s career, “Say Anything…” is one of the best John Cusack chick flick movies ever made and considered by many to be the greatest modern romance movie. The directorial debut of writer-director Cameron Crowe, the film showcases Crowe’s writing and directing talents by featuring brilliant dialogue as well as one of the best performances of Cusack’s career, remaining one of his most memorable films to date.

  2. "Serendipity" The best John Cusack chick flick movie of the past decade, this film follows a couple who share an amazing night, part, and through a sheer act of serendipity, meet again after many years. A charming romantic comedy about the funny side of fate, this film features delightful performances from an enchanting Kate Beckinsale, as well as character actors Eugene Levy, John Corbett, and one of Cusack’s longtime friends and collaborators, Jeremy Piven.

  3. "The Sure Thing" One of the earliest films for actors John Cusack and Daphne Zuniga, this sentimental romantic comedy by acclaimed director Rob Reiner is arguably one of the best John Cusack chick flick movies. Featuring one of Cusack’s most memorable characters, Walter “Gib” Gibson, this expertly crafted road movie chronicles the journey of Cusack and Zuniga as the drive across the country to meet a woman who has been assured by Gib’s friend to be a “Sure Thing,” only to fall in love with each other along the way.

  4. "Must Love Dogs" The third film from “Family Ties” writer Gary David Goldberg, this film follows two people who meet through the internet and features an incredible cast consisting of actors like Diane Lane, Christopher Plummer, Stockard Channing, and character actor Dermot Mulroney. One of the best John Cusack chick flick movies in recent years, this film was panned by critics despite particularly powerful performances by John Cusack and Diane Lane.

  5. "Grace is Gone" The directorial debut of writer-director James C. Strouse, this film remains one of the best John Cusack chick flick movies ever made and was produced by the actor himself. The film follows Cusack as a man whose wife has died in the war in Iraq and, while trying to decide the best way to tell his two young daughters the news, ends up giving the two girls their perfect day. The film features one of the most moving performances of Cusack’s career and, while it received mixed reviews from critics and audiences alike, “Grace is Gone” earned praise for both Cusack and director James C. Strouse when it premiered at the Sundance Film Festival in 2007 and won the Audience Award for Drama.