Although she wasn't appearing onscreen, Coppola stayed in the public eye with various artistic ventures. Her interest in fashion (she interned with Karl Lagerfeld at Chanel while in high school) was employed in film again in 1990 when she added a costume design credit for "Spirit of '76" (produced by brother Roman) to her resume. Coppola's next endeavor was Milk Fed, her own line of designer clothing. Joining the ranks of other "celebutots" like Zoe Cassavetes and Donovan Leitch and musicians like Sonic Youth and the Beastie Boys, Coppola was a noted mover on the Los Angeles/New York young hipster scene, a hot-list favorite often seen on the pages of magazines. She and Cassavetes even hosted their own tongue-in-cheek magazine show "Hi-Octane" (1994), a limited run series aired on Comedy Central in 1995, covering music, fashion and lifestyles. Coppola cemented her status as a consistent pop culture presence, additionally enjoying exposure as a music video star, starting with a cameo role in Madonna's "Deeper and Deeper" and moving up to memorable featured turns in "Sometimes Salvation" by The Black Crowes and "Elektrobank" by The Chemical Brothers. The latter (directed by future husband and fellow auteur Spike Jonze) starred Coppola as a gymnast while the former showed her in the midst of a breakdown. While her turn in "The Godfather, Part III" may have indicated a less than stellar screen presence, she was striking and inherently watchable in this capacity, and generated even more underground buzz.

Coppola began to broaden her range of behind the scenes work, beginning with the 28-minute short "Bed, Bath and Beyond" (shot on video), which she edited and co-directed along with Ione Skye and Andrew Durham. She subsequently produced, wrote and directed the black and white comedy short "Lick the Star" (1998) which screened at festivals and aired on both Bravo and the Independent Film Channel. Now a driven filmmaker, Coppola next endeavored to make her feature debut, and courageously chose "The Virgin Suicides" (2000), Jeffrey Eugenides' atmospheric hit novel about a family of teenage girls dealing with their younger sister's shocking death, told from the point of view of a group of neighborhood boys obsessed with them. Oddly structured, sincerely moving and irreverently comedic, the multifaceted novel was an ambitious choice for adaptation. Coppola deftly handled the intricacies of the source material and captured the spirit of Eugenides' fiction, imparting the undercurrents of both innocent enthusiasm and heartbreaking hopelessness. She set the film in suburban Michigan in the 1970s and managed to steer clear of broad stereotypical era markers, giving this singular and yet transcendent tale an appropriately subtle Everyman air. Starring her "Peggy Sue Got Married" co-star Kathleen Turner as the girls' overprotective mother, James Woods as the defeated father, and hot young players Kirsten Dunst and Josh Hartnett, "The Virgin Suicides" also introduced a cast of newcomers, and following its acclaimed screenings at Cannes and Sundance, would introduce Coppola into the ranks of esteemed new filmmakers.

Indeed, her follow-up film "Lost In Translation" (2003) would catapult her into the ranks of the industry's most respected directors. Working from her own somewhat autobiographical screenplay, Coppola crafted a moody, mesmerizing meditation on alienation set in modern Tokyo, where a slumming 50ish Hollywood movie star (Bill Murray), who is on location filming liquor commercials while avoiding his fading marriage, encounters a drifting twentysomething young wife (Scarlett Johansson) left to her own devices by her career-preoccupied director husband (Giovanni Ribisi, in role much rumored to be not-too-loosely based on Coppola's director husband Spike Jonze, who she divorced shortly after the movie's release). The two loners find a common ground in their alienation and form a strong emotional bond, bordering on romantic love. Although the story is simple and wafer-thin, the dissaffected yet charming characters were involving and the performances (Murray's a career re-definer and Johansson's a major breakthrough) and presentation invited audiences to soak in the film's ambiance. As much a validation of Coppola's enviable taste and aesthetics (she pursued the notoriously elusive and noncommital Murray valiantly for many months before finally persuading him to take on the part) her assured direction and visual style established her as a visionary helmer in her own right, entirely apart from her famous family name, and the film earned an abundance of critical accolades--both mainstream and independent--for both her and the film's stars. Coppola herself took home a Golden Globe for Best Screenplay and became the first-ever American woman nominated for an Academy Award as Best Director. She also was nominated for Original Screenplay and as one of the producers of the film, nominated in the Best Picture category. Because her grandfather Carmine and father Francis each won Oscars, and her Oscar victory in the Original Screenplay Category made the Coppolas the second three-generation family of Oscar winners (after the Hustons).