Keith Chegwin made his screen debut in the 1967 Milo Lewis-directed film ‘The Troublesome Double’ where he played the role of ‘Egghead Wentworth.’ In 1970, he reprised his role as ‘Egghead Wentworth’ in the sci-fi film ‘Egghead's Robot’ directed by Milo Lewis. The film has a 5.0 out of 10 rating on IMDb. He next starred in television series and films like ‘Armchair Theatre’ (1971), ‘Macbeth’ (1971), ‘The Liver Birds’ (1972), ‘Aquarius’ (1972), ‘The Adventures of Black Beauty’ (1972), ‘7 of 1’ (1973), ‘My Old Man’ (1974), ‘Village Hall’ (1974), ‘The Tomorrow People’ (1975), ‘Rule Britannia!’ (1975), and ‘Robin Hood Junior’ (1975). In 1976, he joined the cast of the British children's television series ‘Multi-Coloured Swap Shop’ as a presenter. The show ran for 6 seasons and aired its final episode in 1982. In 1976, Chegwin also became a part of another British children's TV show ‘Record Breakers’ created by Alan Russell. He stayed on the show until 1983. In 1978, he joined the British children's game show ‘Cheggers Plays Pop’ as a host and presenter. The show aired 77 episodes in a span of 9 seasons before going off-air in 1986. He next appeared in films and television shows like ‘Star Games’ (1980), ‘Top of the Pops’ (1981), ‘Aladdin and the Forty Thieves’ (1984), ‘Anything Goes’ (1984-1985), ‘The Saturday Picture Show’ (1985), ‘Children's Royal Variety Performance’ (1985), ‘The Adventure Game’ (1986), ‘Playbox’ (1987), ‘Comic Relief: The Invasion of the Comic Tomatoes’ (1993), ‘The Perfect Match’ (1995), ‘Zig and Zag's Dirty Deeds’ (1996), and ‘The Young Person's Guide to Becoming a Rock Star’ (1998).
In 1999, he starred as ‘Hugh Pimm’ in the British comedy film ‘Whatever Happened to Harold Smith?’ directed by Peter Hewitt. The film currently holds a 40% approval rating on Rotten Tomatoes. The following year, he appeared in the Julian Kemp-directed British comedy film, ‘House!’ The film has a 6.0 out of 10 rating on IMDb. Chegwin continued to appear in television series and films such as ‘Tabloid’ (2001), ‘Fun at the Funeral Parlour’ (2002), ‘Shaun of the Dead’ (2004), ‘Extras’ (2006), ‘The Podge and Rodge Show’ (2007), ‘The Slammer’ (2010), ‘Sooty’ (2011), ‘Life's Too Short’ (2011-2013), and ‘A Gert Lush Christmas’ (2015). He last appeared in the British television quiz show ‘Pointless Celebrities’ in 2016.