Britain's favourite part-Troll funnyman makes up for missing the city out of his career thus far with a whopping six-night stint at the Theatre Royal from Monday.
And if it wasn't for The Man he might never have got to the city at all.
Bill's comedy career was burning so slowly in the early 1990s that he stubbed it out and got a proper job.
"I was selling ad space for an international business management development magazine," he kind-of recalls. "I can't remember its name now, but what's worse is I couldn't even remember its name then, when I was trying to sell its advertising."
The future stand-up refused to take it sitting down when he was ordered to wear a tie, even though he never met customers – he worked in telesales.
"I was thinking, 'The Man ain't gonna tell me what to do. I'm sticking it to The Man – oh, I've been sacked."
A decade on Bill is laughing all the way to being one of the most bankable all-rounders around.
The comedian, musician and actor has enjoyed critical and popular acclaim with his live shows Bewilderness and Part Troll, and had continual exposure for his laid-back style in TV shows such as Never Mind the Buzzcocks, Black Books and Spaced.
Raised in Keynsham, near Bristol (his dad was a GP, his mum a hospital nurse) Bill and his career have always had a hint of the farcical, usually intentional, occasionally unplanned.
He was in a group called The Famous Five – an unsuccessful band with four members – and his comedy double-act show once attracted an audience of one, a fellow comedian who the pair took down the pub and told the jokes to in person over a few drinks.
Bill's perseverance was rewarded when his solo show, Bill Bailey's Cosmic Jam, got universal praise and Channel 4 ran a one-hour special 'live' from the Bloomsbury Theatre in 1996. At last he took off and was able to tie together the music and Pythonesque whimsical rambling gags that are his style.
He picked up a Time Out award, was pipped for the Perrier but bagged the Best Live Stand-Up gong in the British Comedy Awards, 1999. Recognition has allowed him to dip into other projects, including presenting the wildlife show, Wild Thing I Love You, for Channel 4.
Currently he is developing ideas for film and television with his own production company, Glassbox Productions who are responsible for bringing to the screen Tinselworm and Bill Bailey's Remarkable Guide to the Orchestra.
His Bill Bailey: Live tour features much new material as well as including parts of Tinselworm.
He says: "First time for me in Plymouth I think, bigging up the South Coast Massive ... or something.
"So many places, so many tiny individual pots of Milk-Style Dairy Type Liquid."
So why is Bill so good? For starters he is hilarious and unique.
Bill is also versatile and despite the gentle hippie persona can quickfire with the best of them with a wit that is second to none. When one critic complained that his act had no jokes in it, the next night Bill did the Edinburgh show entirely made out of punchlines.
Perhaps the key is that Bill's stand up avoids knocking people down. There is an affection and an inclusivity to his humour which defies the trend towards the sneering and the nasty. As he says of his musical skits: "You have to know the style of the musician really well in order to nail it. So all my tributes have a spark of affection in them."
Catch Bill Bailey: Live from Monday to Saturday next week. Tickets are £25 for Monday to Wednesday, £27.50 for Thursday and Friday and £30 for Saturday; box office: 01752 267222 or www.theatreroyal.com.