Holland debuted in 1982 in a small role of ‘schoolboy’ in Channel 4 film P’tang, Yang, Kipperbang. In 1998 he played “Bob” in The Young Person’s Guide to Becoming a Rock Star. In 1999 he appeared as “Cello Player” in Tube Tales. Holland has written four screenplays, three of which have been sold to producers, but as yet, have not been made into films.

Holland’s first foray into radio was on hospital radio when he joined North Middlesex Hospital’s radio station, Radio North Mid in 1990.

Holland started performing stand-up comedy in 1991, making his debut at The Comedy Café, Rivington Street, London. In 1993, he was briefly managed by Eddie Izzard. In Holland’s first year at the Edinburgh Fringe his one-man show won the Perrier Best Newcomer award and good notices. Later in the autumn of 1993, Holland supported Eddie Izzard on his national tour. In 1994, Holland returned to Edinburgh. In 1996, his show at the Edinburgh festival was nominated for the Perrier Award. Holland returned to the Edinburgh festival in 2006. In October 2012 Holland recorded his first stand up DVD at the Court Theatre in Tring.

Holland made his TV debut appearance in 1993 on Central Television’s Lafter Hours with Harry Hill. He was a team captain for two series of Bring Me the Head of Light Entertainment for Channel Five – with Graham Norton hosting in 1998. In 1999 and 2000, Holland appeared twice as a guest on Have I Got News for You, They Think It’s All Over, and in 2000 The Royal Variety Performance. He has appeared on Rob Brydon’s Annually Retentive. He has been a regular panellist on the daytime debate show The Wright Stuff.

The Small World of Dominic Holland was a radio programme written and presented by Holland, featuring his stand-up work, but including sketches. One series of the show was commissioned in 2000. This was first broadcast on BBC Radio 4 and won a Comic Heritage Award. It has been repeated on BBC 7.

His second radio series on Radio 4, Holland’s Shorts. was a series of comic monologues written and performed by Holland. In 2011 he appeared on Radio 4’s The News Quiz, hosted by Sandi Toksvig. Holland was co-writer of Hal, a 2017 sitcom commissioned by BBC Radio 4, that starred Hal Cruttenden, in which Holland also appeared. He also made regular appearances in the early seasons of BBC Radio 5 Live’s comedy sports panel show, Fighting Talk.

Holland has written material for Bob Monkhouse, Lenny Henry, Harry Enfield, Des O’Connor, Clive Anderson and many others. Holland has published two comic novels, Only in America and The Ripple Effect. His third novel, A Man’s Life, was published in 2013. For two years Holland wrote the Funny Money column for The Guardian. In January 2013 Holland published How Tom Holland Eclipsed His Dad.