Rickman made his film debut as a vicious German terrorist in "Die Hard" (1988) and followed up as Kevin Kline's artsy pal in "The January Man" (1989) and as a tyrannical landowner in "Quigley Down Under" (1990). He made an engaging, if deceased, romantic lead in Anthony Minghella's love/ghost story, "Truly, Madly, Deeply" (also 1990), then went back to evil as a sadistic interrogator in "Closet Land" (1991).

In 1991, Rickman stole the hugely budgeted "Robin Hood: Prince of Thieves" from star Kevin Costner, delightfully tearing into the scenery as the evil Sheriff of Nottingham. He co-starred in the low-budget British drama "Close My Eyes" (also 1991) as a man whose girlfriend has an incestuous relationship with her brother, and was the campaign manager of "Bob Roberts" (1992). In the Irish "An Awfully Big Adventure" (1995), Rickman played the star of a ramshackle repertory theater company. That same year, he was Colonel Brandon, Kate Winslet's dark, smoldering suitor, in the Emma Thompson-scripted, Ang Lee-directed "Sense and Sensibility". Rickman earned an Emmy for the title role in the 1996 HBO drama "Rasputin". He co-starred as Eamon De Valera in Neil Jordan's biopic "Michael Collins" (1996).

By 1998 Rickman had successfully evaded typecasting as a flamboyant villain and sunk his teeth into numerous character roles of varying size. He paired well with Emma Thompson as a pair of detectives trailing bumbling kidnappers in "Judas Kiss" (1998) and played Metaron, an angel who appears inside a pillar of fire only to be doused with a fire extinguisher in "Dogma" (1999), writer-director Kevin Smith's comedic pillorying of religious doctrine, and he reached tremendous comic heights in the "Star Trek"-skewering comedy "Galaxy Quest" (1999) as the bitter, Leonard Nimoy-esque actor Alexander Dane, a serious Shakespearean thespian who resents being typecast in his cheesy sci-fi TV show role as Dr. Lazarus. In "Blow Dry" (2001), an amiable, bittersweet British comedy from "Full Monty" writer Simon Beaufoy and director Paddy Breathnach, Rickman had the lead role, playing former world champion hair stylist who's become a small-town barber taunted for his lack of achievement in competitive hairdressing by his former rival, and who re-discovers an old love when she is diagnosed with cancer.

Rickman next tackled a part which, while relatively small, would make him an icon in the minds of a generation of book lovers and moviegoers when he appeared as the skulking, seemingly malevolent Professor Severus Snape in "Harry Potter and the Sorcerer’s Stone" (2001), a scene-stealing role he would repeat in the film's sequels in 2002 and 2004. He also had a turn in the large ensemble of writer-director Richard Curtis' multi-story comedy "Love Actually" (2003) as a man contemplating being unfaithful to his wife (Emma Thompson), and portrayed the heart surgery-pioneering physician Alfred Blalock in the above-average HBO film "Something the Lord Made" (2004). Rickman generated plenty of laughs when he voiced Marvin, the manic depressive robot with a brain the size of a planet who’s been relegated to menial tasks by his far less intelligent human masters in “The Hitchhiker’s Guide to the Galaxy” (2005), the eagerly awaited film version of Douglas Adams’ popular masterworks of comedy and science fiction.

Rickman again revived his role as the mysterious Professor Snape for the series’ fourth installment, “Harry Potter and the Goblet of Fire” (2005), the first to be helmed by a British director (Mike Newell). Then in late 2005, he began shooting “Zodiac,” a psychological thriller about the famed Zodiac killer who terrorized San Francisco from 1966-1978.