Skinner performed his first stand-up gig in 1987 and made his television debut a year later. In 1990 he co-wrote and starred in the comedy variety show Packet Of Three on Channel 4 but continued to see his reputation as a stand-up grow. Before becoming a full-time performer in 1989, he suffered a bout of influenza in September 1986 that made him give up drinking, and he remains a high-profile recovering alcoholic.
Skinner won the 1991 Perrier Award at the Edinburgh Fringe, beating Jack Dee and Eddie Izzard. He has worked with David Baddiel, notably on the popular late night entertainment show Fantasy Football League, from 1994–2004, and on Baddiel and Skinner Unplanned from 2000 to 2005. The duo also co-wrote and performed the football song "Three Lions" with the Lightning Seeds and the England national football team for Euro 96, and re-released it for the 1998 World Cup. The song reached #1 in the UK charts both times. In 2001, he released his autobiography Frank Skinner by Frank Skinner, which became a bestseller. The accompanying TV show, Frank Skinner on Frank Skinner, in which Skinner showed where he lived as a child and interviews with Skinner, his friends and family members, was recorded and shown on ITV in 2001.