Prior to the 1987 general election, Henry lent his support to Red Wedge by participating in a comedy tour organised by the campaign. But when their mum’s treasured storybook turns out to be a portal to another world full of mythical legends, everything changes. Directed by Destiny Ekaragha, it was a fictionalised account of Henry's life as a teenager in 1970s Dudley. Henry voiced Dre Head, the " shrunken head" on the Knight Bus in the 2004 Alfonso Cuarón movie Harry Potter and the Prisoner of Azkaban, and read the audiobook version of Neil Gaiman's Anansi Boys. The Book of Legends by Lenny Henry Length: 3 hrs and 35 mins was a wonderful and What if all the stories were real?

The audiobook is narrated by Lenny Henry and is vivacious and highly entertaining with Lenny Henry providing a wide array of voices .Henry appeared in advertisements for butter products in New Zealand, commissioned by the company now known as Fonterra, as well as portraying Saint Peter in the Virgin Mobile advertising campaign in South Africa. During this time, he also spent three years as a DJ on BBC Radio 1, playing soul and electro tracks and introducing some of the characters that he would later popularise on television. Henry also wrote, "Because we love you – we want you to be safe and we don’t want you to be left out or left behind. The show featured stand up, spoofs like his send-up of Michael Jackson's Thriller video, and many of the characters he had developed during Summer Season, including Theophilus P. Across the incarnations, he performed impressions of several iconic American celebrities such as Beyoncé, JAY Z, Tina Turner, Prince, Michael Jackson (both men share a birthday date), Stevie Wonder, Run DMC, Cee Lo Green, Denzel Washington, Idris Elba and Wesley Snipes.

Around the same time, he co-hosted the children's programme Tiswas from 1978 until 1981 playing such characters as Rastafarian Algernon Razzmatazz, David Bellamy and Trevor McDoughnut (a parody of Trevor McDonald), and subsequently performed and wrote for the show Three of a Kind.Wherever you are, wherever you're from, whatever race, colour, creed, gender, or sexuality, I say welcome, welcome, and once again, welcome. In 2014, Henry appeared in and produced a play based on his radio show Rudy's Rare Records, which played at the Birmingham Repertory Theatre before moving on to a run in London. Henry studied for an MA at Royal Holloway, University of London in screenwriting for television and film, where he received a distinction and where he is now studying for a PhD on the role of black people in the media. In July 2018, Henry was awarded a PhD in media arts for a thesis titled Does the Coach Have to be Black? K. Audio for a review copy of the unabridged audiobook edition, both via NetGalley, of ‘The Book of Legends: What if all the stories were real?

In June 2000, for a BBC documentary, he sailed a trimaran from Plymouth to Antigua with yachtsman Tony Bullimore.He introduced characters who both mocked and celebrated African Caribbean British culture, such as Brixton pirate radio disc jockey DJ Delbert Wilkins.

He also made guest appearances on television programmes including Celebrity Squares, Seaside Special and The Ronnie Corbett Show. He subsequently studied at the latter institution for a Doctor of Philosophy (PhD) degree on the role of black people in the media. Henry later released "hard-hitting animated blues video" directed by Iranian filmmaker, Sam Chegini titled The Cops Don't Know which was premiered by Classic Rock magazine on 20 April 2016. His formative years were spent in working men's clubs, where his act was as a young black man impersonating white characters such as the Some Mothers Do 'Ave 'Em character Frank Spencer (whom he impersonated on New Faces). and The Magicians for BBC One, and in his later years has transitioned toward acting roles in stage and screen.Henry was criticised for his opening sketch for the 2011 Comic Relief, during which he spoofed the film The King's Speech and grew impatient with Colin Firth's portrayal of King George VI as he stammered over his speech. Henry is associated with the British Comic Relief charity organisation, along with his former wife, comedienne Dawn French, and Griff Rhys Jones, and has hosted the show and also presented filmed reports from overseas on the work of the charity.