Cumming is known for his film roles in Circle of Friends (1995), GoldenEye (1995), Emma (1996), Romy and Michele's High School Reunion (1997), Buddy (1997), Spice World (1997), Eyes Wide Shut (1999), Nicholas Nickleby (2002), The Tempest (2010), Burlesque (2010), and Battle of the Sexes (2017).

He also featured in a comic relief sketch in 1993 on the popular UK television show Blind Date with Atkinson playing Mr.

The series was written by Cumming and co-star Forbes Masson, continuing an acting-writing partnership the two had developed since their drama school days.

American audiences first saw him portraying the smarmy Sean Walsh, an unwanted suitor of Minnie Driver's character, in Circle of Friends, an Irish film released in 1995.

He played Slupianek in the Traverse Theatre's 1988 production of Conquest of the South Pole, which later transferred to the Royal Court in London and earned him an Olivier Award nomination as Most Promising Newcomer.

In 1991, he played The Madman in the 1990 Royal National Theatre production of Accidental Death of an Anarchist by Dario Fo, for which he won the Laurence Olivier Award for Best Comedy Performance.

He gained prominence for his role as The Master of Ceremonies in Sam Mendes's 1993 revival of the musical Cabaret in London's West End opposite Jane Horrocks as Sally Bowles.

He reprised the role in 1998 for the Mendes-Rob Marshall Broadway revival, this time opposite Natasha Richardson as Sally Bowles.

[19] His first film in the United States was 1997's Romy and Michele's High School Reunion, playing Sandy Frink opposite Lisa Kudrow and Mira Sorvino.

[20] Other US stage roles include Otto in the 2001 Broadway production of Design for Living by Noël Coward and Mack the Knife in the Bertolt Brecht-Kurt Weill musical The Threepenny Opera opposite Cyndi Lauper.

Cumming performed alongside Dianne Wiest in Classic Stage Company's production of Anton Chekhov's The Seagull, directed by Viacheslav Dolgachev.

[21] He has also written articles for magazines, notably as a contributing editor for Marie Claire, writing on the haute couture shows in Paris, as well as what it was like for him dressing as a woman for a day.

He has written introductions and prefaces to various books, including the works of Nancy Mitford, Andy Warhol and Christopher Isherwood, and wrote a chapter of If You Had Five Minutes with the President, a collection of 55+ essays by members or supporters of The Creative Coalition.

[23] On 1 September 2009, Cumming released his first solo album based around his one-man show, I Bought a Blue Car Today.

He brought this critically acclaimed[25][26] production of Macbeth to New York's Lincoln Center in 2012 and to a 73-show Broadway engagement at the Ethel Barrymore Theatre in 2013.

That same year he returned again to Broadway to star in Roundabout Theater Company's revival production of Cabaret, directed again by Sam Mendes.

In November 2016, PBS aired a filming of his show Alan Cumming Sings Sappy Songs from The Smith Center in Las Vegas.

The show was named Best Lifestyle Programme at the Emmys' 60th annual awards ceremony at New York's Marriott Marquis Broadway Ballroom.

[35] Alan Cumming was cast as the lead character in the CBS series Instinct, an academic seeking to help the NYPD solve crimes.

[38] In recent years, Cumming has been a regular contributor to the Edinburgh International Festival, with performances including Alan Cumming Sings Sappy Songs in August 2016,[39] Alan Cumming is not Acting his Age in August 2021,[40] and Burn in August 2022: a one-man dance show co-produced by Edinburgh International Festival, National Theatre of Scotland and The Joyce Theater, in which he played Scots poet Robert Burns[41] In 2020, he played in Endgame at The Old Vic, co-starring with Daniel Radcliffe.

[45] Since 2023, Cumming hosts the U.S. version of the reality TV series The Traitors U.S..[46] Cumming has promoted LGBT rights, MC-ing and attending fundraisers for organisations such as the Gay & Lesbian Alliance Against Defamation (GLAAD) and the Human Rights Campaign (HRC), and taking part in an Equality Network video campaign, from New York, promoting the legalisation of same-sex marriage in Scotland.

[48][49] Cumming recorded a duet of "Baby, It's Cold Outside" with Liza Minnelli to raise money for Broadway Cares/Equity Fights AIDS and 11 September Fund.

[51] In October 2023, Cumming signed the Artists4Ceasefire open letter to Joe Biden, President of the United States, calling for a ceasefire of the Israeli bombardment of Gaza.

Cumming was appointed Officer of the Order of the British Empire (OBE) in the 2009 Birthday Honours for services to film, theatre and the arts and to activism for equal rights for the gay and lesbian community in the United States.

[74][75][76] On 27 January 2023, his 58th birthday, Cumming announced via his Instagram page that he had decided to return his OBE due to "misgivings I have being associated with the toxicity of empire".