Crowe moved to the director's chair with "Say Anything" (1989), a superior, insightful study of teen angst finely acted by John Cusack, Ione Skye and John Mahoney as a seemingly perfect father whose exposure as a crook shatters his daughter's world. The equally engaging "Singles" (1992) saw Crowe shift his focus to a slightly older (twentysomething) age group embarking on the adult life in Seattle. Good performances, fine comic timing and a soundtrack featuring the music of Seattle's popular rock scene, however, failed to translate into box-office success.

Crowe waited for four years before returning to the big screen, writing, directing and producing "Jerry Maguire" (1996), a mature examination of the fall and redemption of a flawed but essentially noble sports attorney. Partly inspired by the films of Billy Wilder, particularly 1960's "The Apartment", "Jerry Maguire" opened to excellent notices and a healthy box office. It also provided star Tom Cruise (as Jerry) with one of his best screen roles, tapping a depth and vulnerability rarely seen in the actor's performances. The feature also provided star-making turns for Cuba Gooding Jr (as Jerry's one loyal client) and Renee Zellweger (as the love interest), and introdued a pair of oft-quoted lines of dialogue: "You complete me," and "You had me at hello."

Crowe followed up with a dream project, "Almost Famous" (2000), which followed the adventures of a teenage rock journalist (Patrick Fugit) as he travels with an up-and-coming but also unraveling band and falls for the sweetly seductive groupie--or "band aid," in her parlance--Penny Lane (Kate Hudson). Although fictionalized, the writer-director mined his own life to create a true-to-life portrait of the world of early 1970s music, infused with an affecting tale of self-discovery, first love and disillusionment. While critically acclaimed, "Almost Famous" proved to be somewhat disappointing in its box office but it brought the filmmaker a Best Original Screenplay Oscar and eventually garnered a widespread audience.

Crowe followed by reteaming with Cruise on the off-kilter, reality-questioning "Vanilla Sky" (2001), an Americanized version of the 1998 Spanish film "Open Your Eyes" that, despite a fine performance from Cruise, was a bit too oblique and overly symbolic to be embraced by a mainstream audience. Returning to more "Jerry Maguire"-esque territory, Crowe's next original effort as writer-director was "Elizabethtown" (2005), another romantic, humanistic fable built largely, like "Almost Famous," on Crowe's personal experiences. Inspired by his encounter with a ribald clan of family members in Kentucky he never knew but encountered upon his father's death, Crowe crafted a story around a hotshot young shoe designer (Orlando Bloom) made suicidal by the "fiasco" of his failed multi-billion dollar effort, but finds himself re-examining his despair when, forced to go to Elizabethtown to claim his father's body after an unexpected death, he is warmly received by his distant kin and encounters a beguiling, optimistic flight attendent (Kirsten Dunst) who gives him a new perspective on life. Though over-long and over-reliant on its otherwise impeccable music, "Elizabethtown" was a welcome return to the kind of emotion-fueled, character-driven story Crowe tells so well.

Though known for his sentiment, Crowe was a devoted admirer of the master cynic himself, director Billy Wilder, and after unsuccessfully attempting the veteran into taking a small role as Tom Cruise's mentor in "Jerry Maguire," Crowe struck up a warm but probing relationship with the wily, self-mythologicizing raconteur Wilder that as eventually translated itself into the insightful and often mesmerizing book Conversations With Wilder (2000).