5 Vanilla Sky (2001)
Crowe switched it up with this dark remake of Spanish sci-fi mind bender Abre Los Ojos (Open Your Eyes), and was met with a fair amount of negativity for his efforts. However, in his reteaming with Jerry Maguire star Tom Cruise, Crowe crafted a compelling, challenging film with great work by Cruise, Penelope Cruz (reprising her role from the original), Jason Lee and Cameron Diaz (never better). Cruise portrays a publishing giant with the world at his feet whose life unravels after being disfigured in a car wreck engineered by his unhinged, jealous lover (Diaz). What follows is a lucid nightmare of sorts, where nothing is as it seems, leading to a conclusion that leaves more questions still, depending on how one chooses to look at it. Vanilla Sky is nothing, if not underrated.
4 Jerry Maguire (1996)
As corny as Crowe gets, yet also as inspiring, this 90s megahit/pop-culture phenomenon, won accolades all over, particularly for the work done by stars Tom Cruise, and Cuba Gooding Jr., who won his first Oscar as loudmouth football star Rod Tidwell. Crowe’s script, which has the distinction of being one of the most quoted of all time, tells the story of the sports agent of the title (Cruise), who gets an attack of conscience and nearly loses everything because of it. Maguire takes along secretary/eventual love interest Dorothy (Renee Zellweger) when his firm fires him to start from the ground up, putting everything behind Gooding Jr.’s bombastic second-stringer. Cruise channels his trademark intensity into moments of hilarious desperation and incredulous devastation, making Jerry Maguire’s journey to love and self-improvement imminently watchable.
3 Almost Famous (2000)
Patrick Fugit stars in this smartly written coming of age story drawn from Crowe’s own experience as a teenage writer for Rolling Stone. As one can imagine Crowe’s ever-present love of rock takes center stage here, as Fugit’s William gets to go on tour with fictional rising band Stillwater and takes an eye-opening journey across 1973’s American musical landscape. Standout performances include Kate Hudson as self-styled “Band-Aid” (groupie) Penny Lane, Billy Crudup as heartthrob Stillwater guitarist Russell (who has a much -remembered LSD moment at a fan’s house party, something about “golden gods”), Jason Lee as the obnoxious, bitterly envious lead singer, Philip Seymour Hoffman as legendary rock journalist Lester Bangs (who serves as a sort of mentor to William) and Frances McDormand, who scores many of the film’s best (and most baffling) lines as William’s watchful, dingbat mother. The film’s classic rock soundtrack is something to be reckoned with as well, though the film itself could possibly have done without the tour bus “Tiny Dancer” sing-a-long.
2 Say Anything… (1989)
Never has a hero been so simple and hapless, yet so admirable and true as John Cusack’s Lloyd Dobler.The aspirant kickboxer who dares to date above his high school station is not only one of Crowe’s most endearing protagonists, but his boombox-hoisting pose is the stuff of film legend. Underachiever Dobler pursues pretty, perfect valedictorian Diane (Ione Skye), against the advice of his close friends (including a hilariously bitter Lily Taylor) and much to the chagrin of her soon-to-be imprisoned-for–tax-fraud father (John Mahoney, Frasier’s dad). In addition to containing numerous likeable performances,Say Anything rings true in all its settings, from raging high school parties, to uncomfortable family gatherings, while holding a tone that is unwaveringly sweet without ever once being cloying. Like Fast Times, the film packs another era/demographic appropriate soundtrack for the ages, which includes the Red Hot Chili Peppers and The Replacements.
1 Fast Times At Ridgemont High (1982)
Directed by Amy Heckerling, Fast Times is to high school comedies, as Animal House is to college comedies. That is to say, it is the undisputed, eternal last word. We can start with the indelible characters, such as Sean Penn’s stoner-surfer Spicoli, forever on/behind his own cloud, his exasperated teacher-nemesis Mr. Hand (Ray Walston), and arrogant, snappy dressing hustler Mike Damone (a fast-shooter in more ways than one), among others, all of whom perfectly skate a magical line between cartoonish archetype and utterly believable. And then, there are the timeless teenaged situations (virginity loss, money woes, academic pressure), also deftly handled with the same mix of farce and undeniable realism/recognizability, and who can forget poor Judge Rheinhold’s moment of self-loving shame brought on very reasonably by a wet, slo-mo Phoebe Cates. The soundtrack, which includes The Go-Gos and OingoBoingo, is pure 80’s heaven.
Singles (1992) –This snapshot of the Seattle grunge scene stars Bridget Fonda has appearances from Pearl Jam and Soundgarden, and was indirectly responsible for the creation of the television show Friends. That’s a serious 1990’s pedigree. It’s a decent watch, as well.
That’s Cameron Crowe’s best output, end of story. Anyone shocked at the omission of Elizabethtown or We Bought A Zoo is suggested you watch those particular films again before embarrassing yourself, but if you absolutely insist, you are free, as always, to make your own list.