Amongst these characters was the Greek kebab-seller with markedly fractured English, "Stavros", a profound supporter of the football club Arsenal F.C., which he demonstrated by frequently uttering the phrase "Up the Arse".

His other popular character "Loadsamoney" (an obnoxious character who constantly boasted about how much money he earns) spawned a hit single in 1988 and 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 the "Loadsamoney" was being seen as a positive image and killed him off. In 1989 Enfield realised a personal project with the spoof of British Theatre Knights slumming in the film industry Sir Norbert Smith: A Life.

Before that he provided voices for the British satirical puppet show Spitting Image.

In 1990, Enfield moved to the BBC where he developed his sketch show, Harry Enfield's Television Programme, and later Harry Enfield and Chums with fellow comedians Paul Whitehouse (later of Fast Show fame) and Kathy Burke. This created more nationally recognised characters such as "Mr. and Mrs. Loadsamoney", "Tim, nice but dim" (a character frighteningly similar to the British Conservative politician Boris Johnson), "Smashie and Nicey", "Wayne Slob" and "Annoying Kid Brother" who grew into "Kevin The Teenager". Two characters played by Enfield and Jon Glover, Mr Cholmondley-Warner and Grayson appeared for several years both in the series' mock 1950s information film sketches, and in television commercials for the first of the privatised UK telephone companies, Mercury Communications. Enfield is a professed fan of classical opera and for Channel 4 fronted a documentary series on the subject.

His first sitcom appearance came in 1992, when he played "Dermot" in Men Behaving Badly on ITV. He left after the first series, and was replaced by Neil Morrissey, who played 'Tony' in the subsequent five series, and various one-off specials.

In 2000 Enfield appeared in a his first leading film role playing "Kevin" alongside Kathy Burke, who played the character's male friend "Perry" - roles originally created for the 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 molesting their idol DJ "Eyeball Paul", played by Rhys Ifans, whilst gaining love but losing virginity along the way.

Enfield appearances in commercials have been prolific, including the 1996 run for Dime Bar. (One memorable commercial in this series had Enfield as a country yokel refusing a Dime bar with its crunchy centre because he preferred armadilloes - soft on the inside and crunchy on the outside.) In 2004, he starred in a series of commercials for Burger King in the US as Dr. Angus, a character designed to promote the company's newest hamburger.

After a short break Enfield signed a new contract with BSkyB, but only produced 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 name in Private Eye, as the ageing rockstar character, Gary Bloke.

As of 2004, Enfield provided the voice of "The Roaming Gnome" character used in Travelocity's US advertising campaign.

He has a son and two daughters with his second wife, Lucy.

Harry's father, Edward Enfield, has also made a few appearances as a television presenter on British television.