She began acting at age seven, starring as the male lead in the play "Westward Ho Ho Ho". This gender bending role prepared the young actress to take roles removed from her own experience and since then she never shied away from portraying less-than-likable characters both in film and on television. The Long Island-raised Donovan appeared on the NYC based soap "Loving" after a move to Manhattan and also worked off-Broadway in plays including "Safe" and "Mad Love". Next the actress was off to Los Angeles in 1994, having landed a recurring role on the NBC sitcom "Blossom" playing Tanya, the girlfriend of Joey Lawrence's clueless character.
Donovan scored big screen points as a rival to Alicia Silverstone's Cher in the blockbuster comedy "Clueless"; her strong screen persona made for the perfect Amber, a character whose wild wardrobe could easily outshine an actress with a less dynamic presence. That same year, she increased her industry profile with a more substantial and misanthropic part as the conniving Ginger, a blackmailing, drug using thief in Fox's primetime serial "Beverly Hills, 90210". The redheaded New Yorker proved adept at playing California girls, and was cast in "Encino Woman", a 1996 ABC TV-movie, followed by the regular starring role on the TV series adaptation of "Clueless" (ABC, 1996-97; UPN, 1997-99). Here Donovan's character was now firmly in the forefront of the action, showcased along with Stacey Dash as Dionne and Rachel Blanchard as Cher. While its beginnings were shaky, with low ratings leading to a first season cancellation by ABC, the series found a place at UPN and was a successful addition to the network's "Moesha"-led teen-geared lineup. As Amber, the arrogant, competitive friend of good-natured Cher, Donovan delivered the funniest lines on the program, was put in the zaniest situations, and paraded around in remarkable parodies of eclectic high fashion. While still going strong on "Clueless", the actress made a 1998 film appearance as misguided fortune hunter Cambi in the comedy "A Night at the Roxbury", a full length adaptation of a "Saturday Night Live" sketch featuring a pair of loser brothers in a nightclub. Donovan followed with her first significant role in a non-comedic production in "Loving Jezebel" (1999), shot in her native New York.