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Henson was born on November 3, 1963, in New York City, the third child of Jane Henson (née Nebel; 1934–2013) and Jim Henson (1936–1990). He has four siblings: Lisa (born 1960), Cheryl(born 1961), John (1965–2014) and Heather Henson (born 1970).

As a child, Henson appeared in some of the filmed segments that his father produced for the PBS children's series Sesame Street.

As a teenager, he built the first Muppet penguin puppet for the opening "Lullaby of Broadway" segment of a Season 3 episode of The Muppet Show. During his summer break from high school at the age of 17, Henson assisted in the production of The Great Muppet Caper (1981); skilled in the use of marionette puppets, he helped create and operate a special rigging device that allowed the Muppets to appear to ride bicycles. Several years later, after performing marionette work in The Muppets Take Manhattan (1984) in the scene in which rats cook food in a diner, he specialized in managing complicated special effects.

Henson performed Jack Pumpkinhead in Return to Oz (1985), operated special effects for Santa Claus: The Movie (1985) and was a principal performer for the Audrey II puppet in Little Shop of Horrors (1986), controlling mouth movement while others performed the lips and vines. He also performed the voice of Hoggle, one of the main characters in his father's film Labyrinth(1986), and the dog in both versions of The Storyteller (1988 and 1990).

In 1992, Henson directed The Muppet Christmas Carol and directed the next film in the franchise, Muppet Treasure Island, in 1996. He performed the role of Dr. Phil van Neuter, the Muppet mad scientist character he performed on Muppets Tonight, in Muppets from Space(1999). In 2018, he directed and produced The Happytime Murders, a puppet crime-comedy film for adult audiences.

Henson was the executive producer for several television series: Dinosaurs (1991–94), Aliens in the Family (1996), Bear in the Big Blue House (1997–2006) and Farscape (1999–2003). In addition to assuming an executive producer role, Henson served as the head judge on the 2014 reality television show Jim Henson's Creature Shop Challenge. He performed the roles of Janice and Scooter in the 2002 television film It's a Very Merry Muppet Christmas Movie.

Henson returned to perform Sal Minella, a character he created for Muppets Tonight, in Muppets Haunted Mansion (2021).

Henson is the cocreator, producer and performer for the adult-themed puppet-based variety show Puppet Up! and has played various characters from the show on the British program That Puppet Game Show.

For The Muppet Show Live in 2001, Henson performed his Muppet characters and one of his father's characters, The Newsman, for the first time. He reprised the role for the 2003 video game Muppets Party Cruise.

Henson married Ellis Flyte, costume designer for the 1986 fantasy adventure film Labyrinth, in November 1990. They divorced in 2002. In 2010, Henson married actress Mia Sara. They have one child, a daughter born in 2005.