[8] When Henry was 10 years old, he began spending time with the man who was later revealed to be his biological father, Albert Augustus "Bertie" Green (1927–2004), another Jamaican immigrant with whom his mother had a brief relationship when she first arrived in England from their native Jamaica.

His earliest television appearance was on the New Faces talent show in 1975, aged 16, which he won with impersonations of Frank Spencer, Stevie Wonder and others.

[12] His first manager was Robert Luff, who signed him in 1975 and gave him the opportunity, between the ages of 16 and 21, to perform as a comedian as part of the Luff-produced touring stage version of The Black and White Minstrel Show.

[15] In 1976, Henry appeared with Norman Beaton in LWT's sitcom The Fosters, Britain's first comedy series featuring a predominantly black cast.

Henry also made guest appearances on television programmes including Celebrity Squares, Seaside Special and The Ronnie Corbett Show.

He introduced characters who both mocked and celebrated African Caribbean British culture, such as Brixton pirate radio disc jockey DJ Delbert Wilkins.

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.

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 (based on Teddy Pendergrass) and Delbert Wilkins.

Across the incarnations, he performed impressions of several iconic American celebrities such as Beyoncé, Jay-Z, Tina Turner, Prince, Michael Jackson (the two men shared a date of birth), Stevie Wonder, Run-DMC, Cee Lo Green, Denzel Washington, Idris Elba and Wesley Snipes.

[23] Prior to the 1987 general election, Henry lent his support to Red Wedge by participating in a comedy tour organised by the campaign.

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.

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.

[citation needed] In 1994, The Daily Mail reported that Henry was set to star in a biographical film of Billy Strachan's life titled A Wing and a Prayer, however the script was never turned into a movie.

He appeared alongside performers such as Bill Bailey, Jasper Carrott, Bonnie Tyler, Bobby Davro and the Lord of the Dance troupe.

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.

The programme has an accompanying website of the same name and broadcasts strange, weird and generally amusing online videos and CCTV clips.

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.

In November 2019, it was announced that Henry would guest star in "Spyfall", the two-part opening episode of Doctor Who's twelfth revived series, which broadcast on New Year's Day and 4 January 2020.

[49][50][51] In 2022, Henry was cast in The Sandman as the voice of Martin Tenbones, a magical, doglike creature who appears in the dreams of another character called Barbie.

[52] Henry penned Three Little Birds, a six-part drama series, based on and inspired by his mother's Windrush experience and co-written with Russell T Davies, and first broadcast on ITV and ITVX in October/November 2023.

"[58] 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".

[62] 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.

He worked with a group of musicians including Jakko Jakszyk, lead singer of King Crimson, to produce the album New Millennium Blues.

[64] 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.

(2019), is a memoir that covers his formative years, starting with the arrival of his parents in Dudley, and ending when he began to experience success in the late 1970s.

During a speech at the British Academy of Film and Television Arts in March 2014, he called the lack of minorities "appalling" and he has continued to raise the issue publicly.

[86][87] In July 2016, Henry became the chancellor of Birmingham City University citing his passion to give life changing opportunities to young people from a wide range of backgrounds.

[85][92] Also in 2016, Henry was awarded an honorary doctorate from Nottingham Trent University in recognition of his significant contribution to British comedy and drama, along with his achievements in international charity work.