Henry's first manager was Robert Luff, who signed him in 1975 and gave him the opportunity to perform as part of the Luff-produced touring stage version of The Black and White Minstrel Show. In July 2009, Lenny Henry stated he was contractually obliged to perform and regretted his part in the show.
His earliest television appearance was on the New Faces talent show, which he won in 1975 with an impersonation of Stevie Wonder. The following year he appeared with Norman Beaton in LWT's sitcom The Fosters, Britain's first comedy series with predominantly black performers. His formative years were spent in working men's clubs, where he impersonated mainly white characters such as the Some Mothers Do 'Ave 'Em character Frank Spencer (whom he impersonated on New Faces). He also made guest appearances on television programmes including Celebrity Squares, Seaside Special and The Ronnie Corbett Show.
Lenny Henry in the 1980s
In 1980, Henry performed in Summer Season in Blackpool with Cannon and Ball. He has since said that "the summer season was the first time [he] felt that [his] act had received a proper response from an audience". Around the same time, he co-hosted the children's programme Tiswas from 1978 until 1981, and subsequently performed and wrote for the show Three of a Kind.
Also in 1980, he teamed up with The Comic Strip where he met his wife, comedian Dawn French. She encouraged him to move over to the fledgling alternative comedy scene, where he established a career as a stand-up comedy performer and character comedian.
He introduced characters who both mocked and celebrated black British culture, such as Theophilus P. Wildebeeste (an homage to Teddy Pendergrass using the 'TP' initials), Brixton pirate radio disc jockey DJ Delbert Wilkins and Trevor MacDoughnut (a parody of Trevor McDonald). His stand-up material, which sold well on LP, owed much to the writing abilities of Kim Fuller. 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. He made a guest appearance in the final episode of The Young Ones as The Postman, in 1984.
The first series of The Lenny Henry Show appeared on the BBC in 1984. 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. Wildebeeste and Delbert Wilkins. A principal scriptwriter for his television and stage shows during the 1990s was Jon Canter. The Lenny Henry Show ran periodically for a further 19 years in various incarnations. He performed impressions such as Tina Turner, Prince, Michael Jackson, Stevie Wonder, Run DMC, among others.
Prior to the 1987 general election, Henry lent his support to Red Wedge by participating in a comedy tour organised by the campaign.
In 1987, he appeared in a TV film Coast to Coast. It was a comedy thriller with John Shea about two DJs with a shared passion for Motown music being chased across Britain. The film has a strong following, but contractual problems have prevented it from being distributed on video or DVD.
In the early 1990s, Henry starred in the Hollywood film True Identity, in which his character pretended to be a white person (using make-up, prostheses, and a wig) to avoid the mob. The film was not commercially successful. In 1991, he starred in a BBC drama alongside Robbie Coltrane called Alive and Kicking, in which he played a heroin addict, which was based on a true story.
Also in 1991, he starred in the Christmas comedy Bernard and the Genie alongside Alan Cumming and Rowan Atkinson. Henry is known as the choleric chef Gareth Blackstock from the 1990s television comedy series Chef!, or from his 1999 straight-acting lead role in the BBC drama Hope And Glory. He was co-creator with Neil Gaiman and producer of the 1996 BBC drama serial Neverwhere.
Henry tried his hand at soul singing, appearing, for example, as a backing singer on Kate Bush's album The Red Shoes (1993) and, backed by David Gilmour of Pink Floyd, at Amnesty International's Big 3-0 fund raising concert. He would later say that neither move showed him at his best, and that he felt most comfortable with character comedy. He would occasionally return to singing, performing in small local venues in the West Midlands. Henry returned to the BBC to do Lenny Henry in Pieces, a character-based comedy sketch show which was followed by The Lenny Henry Show, in which he combined stand-up, character sketches and song parodies.
Lenny Henry on Red Nose Day 2005
In 2003, Henry was listed in The Observer as one of the fifty funniest acts in British comedy. In 2004, he was listed in The Sunday Times as the fifteenth funniest black performer of all time. Henry is associated with the British Comic Relief charity organisation, along with his former wife, comedian Dawn French, and Griff Rhys Jones, and has hosted the show and also presented filmed reports from overseas on the work of the charity. He was the voice of the British speaking clock for two weeks in March 2003 in aid of Comic Relief.
Henry voiced the "shrunken head" on the Knight Bus in the 2004 movie Harry Potter and the Prisoner of Azkaban, and read the audio book version of Neil Gaiman's Anansi Boys. He also voiced a character on the children's show Little Robots. 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. In the UK, he used his character of Theophilus P. Wildebeeste to advertise Alpen muesli, and promoted the non-alcoholic lager, Kaliber.
In June 2001, for a BBC documentary, he sailed a trimaran from Plymouth to Antigua, Jamaica with yachtsman Tony Bullimore. His motive was to as he put it, "have one last adventure". In 2005, he appeared in Birmingham, as an act for "Jasper Carrott's Rock with Laughter". He appeared alongside performers such as Bill Bailey, Jasper Carrott, Bonnie Tyler, Bobby Davro and the Lord of the Dance troupe. In 2006, Henry starred in the BBC programme Berry's Way. He did the voice of Dark Nebula in Kirby: Squeak Squad. On 16 March 2007, Henry made a cameo appearance as himself in a sketch with Catherine Tate, who appeared in the guise of her character Geordie Georgie from The Catherine Tate Show. The sketch was made for the BBC Red Nose Day fund raising programme of 2007.
On 16 June 2007 Lenny appeared with Chris Tarrant and Sally James to present a 25th Anniversary episode of Tiswas. The show lasted 90 minutes and featured celebrities discussing their enjoyment of Tiswas as children, as well as appearances from kids and people who had appeared on the original show. In the summer of 2007, he presented Lenny's Britain, a comedy documentary tour made with the Open University on BBC One on Tuesday nights. In late 2007, he hosted a stand-up comedy tour of the UK.
In early 2008, Henry's series lennyhenry.tv was broadcast on BBC One. The programme has an accompanying website of the same name and broadcasts strange, weird and generally amusing on-line videos and CCTV clips. He starred in the Radio 4 show Rudy's Rare Records. On 31 December 2008 and 1 January 2009, he appeared on Jools Holland's Hootenanny on BBC Two, singing part of the song Mercy along with singer Duffy. In January 2009, he appeared on the BBC's comedy show, Live at The Apollo, in which he played host for the night, introducing Andy Parsons and Ed Byrne, where he referred to Wikipedia as "Wrongopedia" for containing incorrect information about his life.
In October 2009, Henry reprised his role of Deakus to feature in comedy shorts about story writing alongside Nina Wadia, Tara Palmer Tomkinson and Stephen K. Amos. He also offers his own writing tips and amusing anecdotes in the writing tips video clip on BBC raw words – story writing. He supplies the voices of both Big and Small in the BBC CBeebies Children's programs Big & Small.
In 2010, Henry produced and starred in a five-part web series for the BBC Comedy website, Conversations with my Wife, about a fictional couple conversing over Skype while the wife is away on business leaving the husband (played by Henry) to hold the fort at home.
In 2008, he became the face of budget hotel operator Premier Inn, and to date continues to star in adverts for them. One of the adverts caused controversy and was banned from children's programming hours. The advert, from 2010, parodied a well-known scene from the film The Shining, with Lenny Henry spoofing the scene originally starring Jack Nicholson, by smashing a door with an axe and then thrusting his head through the door saying: "Here's Lenny."
In 2011, Henry presented a Saturday night magic series called The Magicians on BBC One. The show returned in 2012, however Henry was replaced by Darren McMullen.
In March 2011, he appeared with Angela Rippon, Samantha Womack and Reggie Yates in the BBC fundraising documentary for Comic Relief called Famous, Rich and in the Slums, where the four celebrities were sent to Kibera in Kenya, Africa's largest slum.
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. The Sun reported that the British Stammering Association had branded the sketch as "a gross and disgusting gleefulness at pointing out someone else's misfortune".
In 2014, Lenny 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.
In 2015 Danny and the Human Zoo a ninety-minute film for television was made and shown, written by Henry and directed by Destiny Ekaragha, it was a fictionalised account of the former's life as a teenager in 1970s Dudley.
In February 2009, Henry appeared in the Northern Broadsides production of Othello, in the title role, at the West Yorkshire Playhouse in Leeds, directed by Barrie Rutter, who, before the production opened, said of the decision to cast him: "knives might be out at me or at Lenny. I don't care. This has come about from a completely genuine desire to do a piece of theatrical work. Bloody hell, how long has the Donmar had Hollywood stars going there for £200? He's six-foot five. He's beautifully black. And he's Othello."
Henry received widespread critical acclaim in the role. Charles Spencer in the Daily Telegraph said "This is one of the most astonishing debuts in Shakespeare I have ever seen. It is impossible to praise too highly Henry's courage in taking on so demanding and exposed a role, and then performing it with such authority and feeling." Michael Billington in The Guardian noted "Henry's voice may not always measure up to the rhetorical music of the verse, but there is a simple dignity to his performance that touches one". Lynne Walker of The Independent said of Henry that his "emotional dynamism is in no doubt. The frenzy within his imagination explodes into rage and, finally, wretchedness. It's not a subtle reading but it works powerfully in this context."
Henry has said that he saw parallels between himself and Othello. "I'm used to being the only black person wherever I go...There was never a black or Asian director when I went to the BBC. Eventually I thought 'where are they all?' I spent a lot of time on my own. Things have changed a bit, but rarely at the BBC do I meet anyone of colour in a position of power."
The production was scheduled to transfer to the West End of London from 11 September to 12 December 2009, to be performed at the Trafalgar Studios in Whitehall.
He was introduced to Shakespeare when he made the 2006 Radio 4 series Lenny and Will, which saw him going "in search of the magic of Shakespeare in performance".
In November 2011, Henry made his debut at the Royal National Theatre in London in Shakespeare's The Comedy of Errors, directed by Dominic Cooke, in which he played the character of Antipholus of Syracuse. The production was selected to be broadcast live to selected cinemas worldwide in March 2012 as part of the National Theatre Live programme. Henry's performance gained generally very positive reviews. Paul Taylor in The Independent wrote that "Henry beautifully conveys the tragicomic plight of an innocent abroad."