Enfield appeared in some television commercials before becoming famous, including one made in 1987 for Tetley. Enfield's commercials include a series made in 1996 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. 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.
As a foil to Loadsamoney, Enfield and Whitehouse created the Geordie "Bugger-All-Money" and in 1988 Enfield appeared as both characters during the Nelson Mandela Birthday Tribute Concert at Wembley Stadium. In time Whitehouse and Enfield became disturbed that Loadsamoney was being seen in a positive light, rather than as a satirical figure, and they had him run over during a Comic Relief Red Nose Day show while leaving the studio after presenting host Lenny Henry with "the biggest cheque of the night"—a physically huge cheque for ten pence. Enfield created "Tory Boy", a character which portrayed a young male Conservative MP.
A sample of the character 'Loadsamoney'(Shut Your Mouth and Look at my Wad) is used in the 1989 Game "Blood Money".
In 1990, Enfield developed his BBC Sketch show, Harry Enfield's Television Programme, later called Harry Enfield and Chums, with Whitehouse and Kathy Burke. Eschewing the alternative comedy style prevalent at the time, both versions of the show were indebted to early '70s 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 (TV series) as Little Jim.
In 1997, Enfield married Lucy Lyster and they have three children.
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.
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.
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.
In 2002, Enfield was the first guest on the revamped version of BBC's Top Gear and also appeared on the show on 23 November 2008. Enfield has also narrated various TV documentaries such as the Discovery Wings channel "Classic British Aircraft".
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.
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 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 May 2016 Enfield appeared as Prince Charles in the Channel 4 sitcom The Windsors.
