Born on July 7, 1944, Thomas Winston Maitland (his middle name is a tribute to Winston Churchill) grew up in Neasden, GLC, Borough of Brent, where his father was an actuary and in the Merchant Marine and his mother was in the RAF. After a failed stint as a pipe fitter's apprentice, Tommy joined the British Army at the tender age of 15. He later joined the Entertainment National Service Association (ENSA), where he got to know some of the UK's biggest comedians. He played the ukulele, told jokes and drummed (though he drummed badly), and he ended up hosting the show - a talent he would later be known for. He was voted ENSA Entertainer of the Year, for which he was given a guarantee to appear on British radio. He later worked as an announcer for the British radio show, "The Whosey Whats," and got small roles in the "Carry On" films – either as the over anxious compart at a men's club or the strict union pipe fitter. He also appeared in the TV series, "The Lord Mayor," as the cheeky mayor of a mythical town in East Anglia, who struck it rich because they sat atop an oil field.
In 1973 Tommy wrote a book about his time in the British Army fighting the Mau Maus, called "The Mau Maus are Revolting," and he also worked at a Butlin's Holiday Camp at the same time, for two seasons, in Anglesea, Wales and Brighton.
Hugely popular in Italy, he made four of his 11 films there. Two of the four were Spaghetti Westerns, where he played the fastidious banker, and the other two were James Bond knockoffs – "You Only Live Once, To Be Honest" and "From Russia, Luv." At the same time, Tommy continued to work the working men's clubs across England, where he received top dollar as an emcee.
In 1976 Tommy starred in "He Wore a Dustman's Hat," about an upper-class city of London gent who discovers that his dad (Tommy Maitland) is a garbage worker for the Council in Hackney. This show played on Canadian TV at 4am on Saturday mornings. Will Arnett saw this show in syndication on Canadian TV in 1980 and thought that Tommy was a comedic genius. Later that year Tommy bought an estate in Kent, called Serendipity, which he found by accident. Serendipity was a mega-celebrity hangout where people could escape, party, do or be anything they wanted to be, free from judgment and the prying eyes of the paparazzi.
In the '80s, Tommy hosted the British game show "Tell You What," which was a charades based adventure game. He later hosted an Australian game show called "Dingo's Got the Baby," in which one contestant would be the Dingo, and one contestant would be the Baby, and a chase would ensue. In 1990 he returned to England for a series of one-hour specials, called "You've Still Got No Proof."
Tommy retired at the age of 55 but was still doing ENSA gigs. He loves comedy, so he often went to the Edinburgh Fringe Festival to watch young comics. Will Arnett, who was doing stand-up at one of the festivals, approached and befriended him. Desperately wanting to work with Tommy, Arnett tried for years to come up with a gig that was suitable for his immense talent, and "The Gong Show" was the perfect match.