Enfield first came to public attention when appearing on Channel 4's Saturday Live as a number of different characters created with Paul Whitehouse. These quickly entered the national consciousness. Among these characters were Stavros, a Greek restaurant owner with markedly fractured English; Tory Boy, a pompous Conservative MP; and Loadsamoney, an obnoxious character who constantly boasted about how much money he earned. Loadsamoney spawned a hit single in 1988 and a sell-out live tour. 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.
In 1989 Enfield realised a personal project, Norbert Smith - A Life, a spoof on British theatrical knights slumming in the film industry. He also provided voices for the British satirical puppet show Spitting Image.
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 yow", 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 BBC presenters, Mr Cholmondley-Warner and Grayson.
In 1991 Enfield played Dermot in the sitcom Men Behaving Badly, originally on Thames Television. He left after the first series and was replaced by Neil Morrissey as Tony. Enfield is a professed fan of opera and fronted a Channel 4 documentary series on the subject.
After a short break from television Enfield signed a new contract with BSkyB, but produced only one series, which flopped badly. 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. The timing was unfortunate for Enfield as almost simultaneously The Osbournes began on MTV, having been a sleeper hit in the United States. The Osbournes, depicting the dysfunctional and unconventional family life of the heavy metal singer Ozzy Osbourne, was effectively what Enfield was trying to satirise with Celeb. The Osbournes became successful in Britain, while Enfield's show disappeared quietly after only six episodes.
In 2002 Enfield was the first guest on the revamped version of BBC's Top Gear. He came in at an "achingly" slow time of 2:01 . Enfield has also narrated various TV documentaries such as the Discovery Wings channel 'Classic British Aircraft'.
In 2007 he played Mr Stoneham in the Channel 4 series Skins.
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.
Enfield appeared in some television commercials before becoming famous, including one made in 1987 for Heineken. Enfield's most memorable 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 2002 Enfield starred in a series of commercials for Burger King in the U.S. 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. In 2004 Enfield provided the voice of "The Roaming Gnome" character used in Travelocity's U.S. advertising campaign.
In 2007 Enfield reunited with Paul Whitehouse for the BBC's Ruddy Hell! It's Harry and Paul, which has a particular emphasis on the British class system. The second season of the series, retitled Harry and Paul, began in September 2008. The show retains its most popular characters, such as the Posh Scaffolders, I Saw You Coming and Pik the bumbling South African, while attacking pop culture on a more regular basis. The satirisation of contemporary Britain continues to be the main basis for the series, with references to popular internet memes, the Apple iPhone and the elderly's alleged tendency to purchase cars produced by Toyota.
Enfield was selected by Dirk Maggs to play Dirk Gently on BBC Radio 4. He has also recently made a documentary, Harry Enfield's Excellent Adventure, in which he followed the route of the German Army during Operation Barbarossa in 1941.
In October 2008 Enfield was accused of racism by the Philippine government . The claim involved a skit on the BBC show Harry And Paul where a man encouraged his pet northerner to "mount" his Filipina maid.
When Ali G Went to Kazakhstan (or How a Cult Comedian Fell out with an Entire Country) ; Trouble Is Brewing Down at the Kazakhstani Embassy. the First Secretary Is Up in Arms over a New Character from Da Ali G Show. He's Already Complained to Channel 4. and Now He Wants to Tell the World What His Homeland Is Really Like
Apr 26, 2000; The Kazakhstani embassy is a pokey diplomatic hidey-hole just a stone's throw from London's Victoria & Albert Museum. Its...