Douglas essayed a small role for Irwin Winkler's McCarthy-era drama "Guilty by Suspicion" (also 1991, in which Scorsese acted), played the fussy eater among the plane crash survivors in "Alive" and brought a fine puppy-like frenzy to her ambitious secretary trying to stay away from men in the enjoyably tacky, no-budget "Grief" (both 1993), a backstage look at the creation of a shameless, tabloid TV show ("The Love Judge"). That year also saw her as a member of the large boisterous Italian family in Nancy Savoca's "Household Saints" (1993), although a significant portion of her scenes ended up on the cutting room floor. Douglas played a bit (as did Scorsese) in Robert Redford's "Quiz Show" (1994) and was sexily charming as an aspiring screenwriter and mistress to a self-help expert (Dennis Hopper) in the low-budget "Search and Destroy" (1995), co-produced by Scorsese. But she really attracted critical and popular attention that year in Gus Van Sant's "To Die For". As the sharp-tongued, ice-skating, lesbian sister of Matt Dillon, she pegged her brother's cable weathergirl wife Nicole Kidman as a phony from the get-go and, when he turned up dead, remained adamant about her sister-in-law's guilt in the Buck Henry-scripted, satiric black comedy.
A self-professed feminist who refreshingly exclaims in the same breath that she's boy crazy, Douglas made the perfect soul sister for writer-director Allison Anders, playing her highest profile part yet as the Carole King-like songwriter-singer of "Grace of My Heart" (1996), a rock musical drama executive produced by Scorsese (their last collaboration to date). Her winning portrayal of one woman's epic drive to find her voice in the male-dominated music industry of the 50s and 60s was the centerpiece of Anders' picture, which in its attempt to cover too much historical ground (from the waning days of Tin Pan Alley at the Brill Building in the 50s and 60s to the psychedelic 70s) tended to drag to its bittersweet conclusion. Still, the acting across the board, particularly a strong performance by John Turturro as a record producer, was a strong focal point throughout, and the director's decision to use new sound alike tunes from the era, penned by such contemporary artists as Burt Bacharach-Elvis Costello (in their first teaming), Carole Bayer Sager and Los Lobos, proved the film's greatest asset.
Douglas made a strong showing in the Eve Ardenesque role of a corporate cutthroat and best friend of Jennifer Aniston in the predictable but pleasant romantic comedy "Picture Perfect" (1997), and she was back in best friend mode for the formula tearjerker "Message in a Bottle" (1999), providing some great moments as gal pal to Robin Wright Penn. A favorite of indie directors, she was memorable in "Happy, Texas" (also 1999) as a teacher, whose bad taste in clothes was equal parts aesthetic and political statement, and also contributed a cameo to that year's "Can't Stop the Dancing".
Douglas made her TV acting debut in a 1995 guest-spot on the NBC series "Homicide: Life on the Street" and also portrayed Jonathan Silverman's abrasive, on-again/off-again girlfriend Martha during the 1995-96 season of "The Single Guy" (NBC). 1997 small screen credits included the Larry Gelbart-scripted HBO movie "Weapons of Mass Destruction", the CBS miniseries "Bella Mafia" and the TNT miniseries "Rough Riders", in which she provided a much-needed female presence, shining graciously as Teddy Roosevelt's wife Edith. Her much touted role as a former child star turned hooker turned studio excutive in "Action" (Fox, 1999) earned kudos from critics but viewers stayed away and the series met an early demise.
Douglas, who believes she would have flourished in the old studio system of the 30s, claims she became a director in self-defense so that she could showcase her neglected comedic side. She scripted (as well as acted in) her first comedy short "The Perfect Woman" (1993), a nine-minute satire eavesdropping on 30 women all trying to be "perfect," and the 30-minute documentary "Everybody Just Stay Calm--Stories in Independent Filmmaking" (Independent Film Channel) featured her as executive producer, director, writer and host. She then returned to comedy for the 21-minute "Boy Crazy, Girl Crazier" (1995), writing, directing and starring as one of two desperately ambitious Hollywood hopefuls who manage to hilariously turn the tables on one another in a matter of minutes. She has not directed since, perhaps because there is no shortage of roles for the constantly working actress. Unfortunately, director John McNaughton and screenwriter David Mamet underutilized her as Meyer Lansky's first wife Anna in the 1999 HBO biopic "Lansky". Nonetheless, the busy Douglas offered able support to Kevin Bacon and Liza Weil in David Koepp's "A Stir of Echoes" (1999) and Madonna and Rupert Everett in John Schlesinger's "The Next Best Thing" (2000).