Cumming had previously essayed the role to acclaim on the London stage in 1993 opposite Jane Horrocks, the same year he gave an extraordinary performance as "Hamlet" opposite his former wife Hilary Lyon's Ophelia. The Scottish actor who first gained fame with a cabaret and Glasgow as half of the campy posh duo "Vic and Barry" starring alongside comedian Forbes Masson, made his London debut with 1988's "The Conquest of the South Pole" (beginning its run in Edinburgh). He went on to win an Olivier Award for his comedic role in "Accidental Death of an Anarchist" (1991) and followed that success with a turn in David Hirson's "Le Bete.”

The actor made his film debut with Gillies MacKinnon's student film "Passing Glory" in 1986. Busy on stage and television, Cumming didn't return to the big screen until six years later with "Prague", starring in this drama as a man in search of a piece of film featuring his family being taken to a concentration camp. Next, he lent his gentle voice to the titular horse in "Black Beauty" and played a social worker alongside Jane Horrocks in the adoption drama "Second Best" (both 1994). He made his directorial debut with the 1994 short film "Butter", starring Lyon as a woman suffering from an eating disorder. Another 1994 short film, Dan Zeff's "That Sunday" paired him with Minnie Driver, who would next co-star with him in the following year's "Circle of Friends". In this charming romance, Cumming played a perfect villain, the oleaginous Sean Walsh, a creepy and overconfident character who, in a bid to take over her father's business, woos an uninterested Benny (Driver). That same year the actor was featured in the Bond film "GoldenEye" as a sinister Russian computer wizard. (Driver also had a small part as a Russian in the spy film.)

In 1996, Cumming starred as the smarmy Reverend Elton in "Emma,” unsuccessfully pursuing the title matchmaker, who had someone else in mind for him. His role as school nobody turned multi-millionaire Sandy Frink matched him with a pair of well-meaning but clueless best friends (Mira Sorvino and Lisa Kudrow) in 1997's "Romy and Michele's High School Reunion". That same year saw Cumming's portrayal of an assistant to an eccentric millionaire placed him alongside Rene Russo, Robbie Coltrane, a gorilla and several chimps in the heartwarming "Buddy" as well as a role in a far different film, playing a Jewish stand-up comedian taken over by the ghost of his sister, a woman murdered in the Holocaust in the disturbing psychological drama "For My Baby" (screened at the Netherlands Film Festival). He followed up with a featured role in the campy mock rockumentary "Spice World" (1998).

After his highly successful "Cabaret" run, Cumming appeared as a flirty hotel clerk in the late director Stanley Kubrick's long-awaited "Eyes Wide Shut", and was also featured as the licentious dandy Lord Rochester, moneyed old friend of Jonny Lee Miller's Macleane in the highwayman action film "Plunkett and Macleane" (both 1999). Fellow toast of Broadway Julie Taymor directed Cumming in "Titus", her 1999 adaptation of Shakespeare's "Titus Andronicus", before the actor was aptly cast in the live-action feature "The Flintstones in Viva Rock Vegas" (2000) in a dual role as the wise and droll little Martian The Great Gazoo and the rock star Mick Jagged.

Cumming further fattened his resume with a string of diverse projects in 2000, appearing in Sly Stallone's actioner "Get Carter" and taking a supporting role as a gay man struggling with AIDS in "Urbania". That same year, he signed on to two fascinating films, as well. He agreed to co-write, co-produce, co-direct and co-star in the film "The Anniversary Party" (lensed 2000), with his "Cabaret" co-star and friend Jennifer Jason Leigh. The movie, which marked Cumming's feature film directorial debut, examined what happens when a couple reconcile after a one-year separation and celebrate their reunion with an anniversary bash that quickly deteriorates into an X-rated game of truth or dare. Cumming also agreed to star as young Adolf Hitler in "Hoffman,” a film that investigates Hitler's relationship with a Jewish art teacher who failed to encourage the future Nazi leader's artistic abilities. 2001 saw the actor paired with Antonio Banderas in the family comedy "Spy Kids" and in a featured role in Alan Rudolph's period comic drama "Investigating Sex.”

Cumming has additionally done impressive work on television, starring along with comedian Lenny Henry in the memorable 1991 TV-movie "Bernard and the Genie" (released in the USA on video the following year), as well as taking roles in "The Last Romantics" and "Mickey Love.” In 1995, he co-starred and co-wrote, along with previous collaborator Forbes Masson, the BBC-2 series "The High Life,” a comedy following the misadventures of a group of Air Scotia stewards. In 1999, he starred on US television as the colorful villain Rooster in the ABC remake of the musical "Annie,” following that up by supplying the animated character of Satan with a voice on the controversial, short-lived NBC comedy "God, the Devil and Bob.” Cumming next revived Fegan Floop, former bad-guy now turned good-guy, for “Spy Kids 2: The Island of Lost Dreams” (2002), then provided a few laughs in “Nicholas Nickelby” (2002) as a frustrated thespian prone to showing off his kilt in this competent adaptation of Charles Dickens’ novel.

Cumming was then tapped by director Bryan Singer to join the ensemble cast of “X2: X-Men United” (2003), playing the evil Nightstalker, a blue teleporter who tries to assassinate the President of the United States (Cotter Smith) in an effort to help lure Professor Xavier (Patrick Stewart) and his mutants into a trap set by the sinister William Stryker (Brian Cox). For his part, Cumming had to constantly wear blue body paint, which caused him to sweat blue, or blow blue through his nose, days later. His suffering was worth it, however, as “X2” did better—critically and at the box office—than its predecessor. Meanwhile, he revived Fegan Floop for a brief appearance in “Spy Kids 3-D: Game Over” (2003). After supplying the voice of Persnickety in “Garfield” (2004), the combination live-action and animated feature based on the long-running comic strip by Jim Davis, Cumming made the rare appearance on television, playing Mark Bodine in TNT’s remake of Neil Simon’s romantic comedy, “The Goodbye Girl” (2004).

For his next project, “Reefer Madness” (Showtime, 2005), a musical parody of the 1936 propaganda film of the same name about the supposed dangers of marijuana use, Cumming donned several on-screen hats—as a lecturer/narrator constantly inserting himself into the cautionary tale about a pair of straight-laced high school students (Kristen Bell and Christian Campbell) who run into trouble when seduced by Cannabis sativa; as a policeman who also lectures on the ill-effects of the Devil Weed; and as the 32nd President of the United States, Franklin D. Roosevelt. He next starred in the unnecessary sequel, “Son of the Mask” (2005), playing the mischievous Norse god Loki sent to Earth on a quest to find the ancient mask or suffer the penalty of becoming mortal. Meanwhile, Cumming used his voice talents in the animated children’s tale, “The Ant Bully” (2006).