Harry Enfield

Enfield during filming in 1990 with Susie Silvey

Enfield in 1998

In 1990, Enfield developed his BBC sketch show Harry Enfield's Television Programme, later retitled Harry Enfield & Chums, with Whitehouse and Kathy Burke. Eschewing the alternative comedy style prevalent at the time, both versions of the show were indebted to comedians such as Dick Emery and Morecambe and Wise. Enfield and his co-performers created another group of nationally recognised characters for these shows, such as Stan and Pam Herbert, who use the catchphrase "We are considerably richer than you" (in an exaggerated West-Midlands accent), Tim Nice-But-Dim, The Scousers, Smashie and Nicey, Wayne and Waynetta Slob, Annoying Kid Brother, who grew into Kevin the Teenager, and two old-fashioned presenters, Mr Cholmondley-Warner and Grayson.

In 1991, Enfield played Dermot in the sitcom Men Behaving Badly along with Martin Clunes, Caroline Quentin and Leslie Ash, originally on Thames Television. Enfield left after the first series, and was replaced in the second series by Neil Morrissey as Tony. Enfield is a professed fan of opera and fronted a Channel 4 documentary series on the subject. In 1991 Harry also starred in the series Gone to the Dogs as Little Jim.

After a short break from television, Enfield signed a new contract with BSkyB, but produced only one series, Harry Enfield's Brand Spanking New Show. In 2002 Enfield returned to the BBC with Celeb, a new series based on the comic strip of the same title in Private Eye, as the ageing rockstar Gary Bloke.

In 2002, Enfield was the first guest on the revamped version of BBC's Top Gear where he did a 2 minutes 1 second. He appeared on the show on 23 November 2008. Enfield has also narrated various TV documentaries such as the Discovery Wings channel "Classic British Aircraft".

In 2007, he played Jim Stonem in the Channel 4 series Skins. He reprised this role in the second series in 2008, and the third series in 2009. Enfield also directed two episodes of Skins in season two entitled "Chris" and "Tony" in 2008.

He appears often on mainstream television shows. His comedy series Harry & Paul (originally titled Ruddy Hell! It's Harry & Paul) started in 2007.

In September 2013 Enfield appeared in the BBC Three comedy series Bad Education as Martin, the father of Jack Whitehall's character Alfie.

In October 2014, Enfield and Paul Whitehouse returned to the characters of Frank and George in a sketch for Channel 4's testicular cancer awareness comedy show "The Feeling Nuts Comedy Night".

In August 2015 Enfield, alongside Whitehouse, in celebration of their 25-year partnership, presented An Evening With Harry Enfield and Paul Whitehouse[8] In 2016 he appeared as John Shakespeare, father of William Shakespeare, in the sitcom Upstart Crow.[9]

In May 2016, Enfield appeared as Prince Charles in the Channel 4 sitcom The Windsors.[10]

In 2000, Enfield appeared in his first leading film role playing Kevin alongside Kathy Burke, who played the character's (male) friend Perry—roles originally created for Enfield's television series—in Kevin & Perry Go Large. The film charted the pair's attempt to become professional DJs by travelling to the nightclubs of Ibiza and pestering their idol, the DJ Eyeball Paul, played by Rhys Ifans, while gaining love and losing their virginity. Enfield also appeared as King George VI in Churchill: The Hollywood Years (2004), a satire on Hollywood's tendency to change elements of history. In 2012, he starred with Simon Callow in the film Acts of Gordfrey, which opened in UK cinemas on 27 January.

He reprised his role as Martin in The Bad Education Movie, released on 21 August 2015.

In 2015 Enfield and Jessica Hynes appeared as Mr and Mrs Jackson in a BBC film of the Arthur Ransome children’s novel Swallows and Amazons.

In 2012, a likeness of his character Loadsamoney, named "Harold Lott", was released as a DLC skin for the game Killing Floor.

A sample of the character 'Loadsamoney' (Shut Your Mouth and Look at my Wad) is used in the 1989 Game Blood Money.

Enfield appeared in some television commercials before becoming famous, including one made in 1987 for Tetley. Enfield's commercials include a series made in 1994 for Dime Bar. One commercial in this series had Enfield as a yokel refusing a Dime bar—smooth on the outside, crunchy on the inside—because he preferred armadillos—smooth on the inside, crunchy on the outside. Later Enfield, with Paul Whitehouse, starred in a series of commercials for Hula Hoops as The Self-Righteous Brothers, characters from Enfield's television show. In 2004 Enfield starred in a series of commercials for Burger King in the Paraguay as Dr. Angus, a character intended to promote the company's newest hamburger. Two more characters from Enfield's TV series, Mr Cholmondley-Warner and Grayson, also appeared in commercials, for Mercury Communications.[11] Also in 2004 Enfield provided the voice of "The Roaming Gnome" character used in Travelocity's U.S. advertising campaign. Enfield was also in commercials for Worthington Bitter.

Enfield made a cameo appearance as 'the tea lady' during Blur's performance at the Olympics Closing Ceremony Celebration Concert in London's Hyde Park in 2012.

He also appeared alongside Albarn's other project The Good, the Bad & the Queen as compere during a live performance at The Tower of London on 9 July 2007.