Director Cameron Crowe was a bit of an outcast in his youth; his mother, recognizing his potential bumped, him ahead two grades in elementary school, which significantly made him the youngest person in his high school. He also suffered from various health issues as a child, which further cemented his outcast status. As a way of coping with being an outsider, Crowe immersed himself in his two passions: writing and music. By age 13, Crowe began writing music reviews for an underground paper called The San Diego Door, which eventually led to a gig as a contributing editor (and eventual associate editor) at Rolling Stone Magazine.

In 1977, however, Crowe decided to focus on a book he was writing about teens coming of age in the 1980s. This was the first stepping stone on his path towards becoming a successful screenwriter and film director. As research for his novel Fast Times at Ridgemont High , Crowe re-enrolled in high school. The book later became a bestseller and the screenplay adaptation for Amy Heckerling’s directorial debut of the same name. Crowe has since written and directed many successful films throughout his lengthy career. If you are a fan of the acclaimed director, you are in luck: we have compiled a list of his best movies, ranked in order of popularity.

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7 Elizabethtown (2005)

     Paramount Pictures

While Elizabethtown may be a controversial pick for the best-of list, due to its reputation as a critical and commercial flop, it is a vastly underrated movie that explores tough topics, like suicidal ideation, death, the grieving process, and the human condition. There is just something about how the characters are written that you cannot help rooting for them. Elizabethtown follows Drew Barton (Orlando Bloom) who has just lost his job after his latest shoe design was a huge flop. He is struggling with suicidal thoughts until his mother calls to tell him his father has passed away and assigns Drew the task of collecting his body. En route to Elizabethtown, he meets a quirky flight attendant named Claire (Kirsten Dunst) which is where the story really begins.

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

MOVIEWEB VIDEO OF THE DAY

6 Vanilla Sky (2001)

Vanilla Sky is a remake of the Spanish foreign film Abre Los Ojos. The film unravels in the form of flashbacks by the main character David Aames (Tom Cruise) while in sessions with a court-appointed psychologist (Kurt Russell). While David recalls his memories, he is wearing a prosthetic face mask. He recounts his most recent memory of spending the night with a woman named Sofia (Penélope Cruz) at her apartment and falling in love with her. When he leaves the following morning, a jilted ex-lover Julie (Cameron Diaz) is waiting for him. She entices him to join her in her car, which she promptly drives off a bridge in a bid to punish David. From that point on, it is difficult to discern dreams from reality, as David tries to make sense of his current circumstance.

5 Singles (1992)

     Warner Bros.

Singles is a quintessential 90s-era movie in the same class as Empire Records or Reality Bites. It is set in grunge-era Seattle and follows the lives of a group of twenty-somethings that inhabit the same apartment building. The movie humorously explores the group’s search for love and the mind games they encounter along the way. It stars Bridget Fonda, Matt Dillon, Kyra Sedgwick, and Campbell Scott. If you are a fan of grunge music, the soundtrack to this film will not disappoint.

4 Say Anything (1989)

     Gracie Films

Say Anything is a critically acclaimed movie about optimistic underachiever Lloyd Dobler (John Cusack) who seeks the affections of the prettiest girl in school Diane Court (Ione Skye), who also happens to be the class Valedictorian. To everyone’s amazement, Diane returns Lloyd’s affections. Her domineering father (John Mahoney), however, does not share the sentiment. The movie follows the couple and the obstacles they must overcome to stay together. The film inspired a TV series that was ultimately shelved when Cameron Crowe disapproved.

3 Jerry Maguire (1996)

     Tri-Star Pictures

Jerry Maguire follows a successful sports agent who has a moral epiphany and pens a mission statement, stating clients are more important than money. When Maguire (Tom Cruise) is promptly fired for growing a conscience, single parent Dorothy Boyd (Renee Zellweger) joins him in his new endeavor. Jerry decides to evaluate his theory and start his own agency; however, he only manages to land one high-profile client, football hot-shot Rod Tidwell (Cuba Gooding Jr.). Along the way, Maguire slowly embodies his philosophy as he begins to see what really matters in life.

2 Fast Times at Ridgemont High (1982)

     Universal Pictures

Fast times at Ridgemont High is based on Cameron Crowe’s first novel of the same name. It follows a group of high school students in Southern California in the ’80s and their misadventures while seeking out love, sex, and a good time. Sean Penn stars in his most well-known role as stoner surfer Jeff Spicoli who is perpetually at odds with his history teacher Mr. Hand. Fast Times was to the 80s what Dazed and Confused was to the 70s, and was an instant critical and commercial success. According to Rotten Tomatoes Critical Consensus, “Fast Times at Ridgemont High endures because it accurately captures the small details of the school, work, and teenage life."

1 Almost Famous (2000)

     Columbia Pictures

Almost Famous is a semi-autobiographical account of Cameron Crowe’s experiences as a teenage writer for Rolling Stone Magazine. The movie boasts an all-star cast including Kate Hudson, Billy Crudup, Patrick Fugit, Jason Lee, Fairuza Balk, Anna Paquin, Zoe Deschanel, Francis McDormand, and the late Philip Seymour Hoffman. It tells the story of 15-year-old child prodigy William Miller (Fugit), who aspires to be a rock journalist despite his disapproving mother (McDormand). Miller is hired by Rolling Stone to write an article on the band Stillwater and goes on tour with them. Once he joins the inner circle William is unable to maintain his objectivity as he forms relationships with his subjects. The film was a critical hit and won Crowe an Academy Award for Best Adapted Screenplay. Almost Famous turned twenty-one this year.