Tom Hibbert, a former Observer columnist and mainstay of both Smash Hits and Q magazines, has died aged 59, from complications brought about by diabetes. His cavalier humour and softly ruthless interview technique earned him a wide following in the pop-culture publications of the 1980s and 90s, as well as the affection and respect of his colleagues.

The son of the historian Christopher Hibbert, Tom was born in Henley-on-Thames, Oxfordshire, and went to Leighton Park Quaker school in Reading and then the local grammar, but dropped out of Leeds University after a term to play in various uncelebrated rock bands and chance his arm as a journalist.

Tom was unsuited to the home-improvement periodicals for which he wrote in the late 70s, but in 1980 his droll and quizzical reviews began to appear in New Music News, an underground rock weekly launched by Felix Dennis to fill the vacuum left by the strike-bound NME and Melody Maker. Tom admired very few musicians beyond Iggy Pop, Ray Davies and Jerry Garcia but filed fond, waspish and lightly mocking deconstructions of many others. Asked by another staff member why he made up all the entries in the short-lived publication's letters column, his response was flatly logical: "Because we don't have any readers."

At Smash Hits in the mid-80s, he helped invent a cartoon fantasy world in which everyone interviewed seemed to exhibit the same slapstick characteristics. All his subjects – Paul McCartney, David Bowie, Bucks Fizz, John Lydon – were delightfully over-exaggerated, as mischievous and eccentric as their interrogator. The magazine was so successful that even the prime minister, seeking re-election in 1987, believed she could speak to the entire nation's teenage youth by allowing Hibbert and his ancient tape-recorder through the door at Downing Street.

Margaret Thatcher's undoing was to attempt to prove that she, too, was a pop-music enthusiast. Tom took great delight in revealing that her favourite singer was Cliff Richard, whom she admired for being professional, and that her favourite record – on-message for the cost-conscious curator of an economic boom – was the fearful 1953 novelty hit (How Much Is) That Doggie in the Window?

Tom was unafraid of silence. He would give his subjects the impression that, despite their obvious successes, they were still somehow shameful underachievers, and then sit back quietly with a cigarette to enjoy the panicked response. Both in work and life, he refused to take anything seriously. When given the job of writing the "trail" to flag up the contents of the next Smash Hits, he would advertise groups that existed only in his fertile imagination – such as the failed pop idol Reg "Reg" Snipton or an intriguing electronic duo, The Human Saucepans of the Orinoco.

Hibbert was transferred in 1986 to the new rock monthly Q, where a long-running feature known as Who the Hell … was devised especially for his withering humour and his extraordinary ability to get pompous public figures to make buffoons of themselves.

Month after month, the gullible and self-important celebrities of the day – Jeremy Beadle, Jeffrey Archer, Robert Maxwell, Samantha Fox, Keith Floyd, Bernard Manning, David Mellor, Sir Jimmy Savile – would find their pearls of wisdom gently lampooned and their carefully constructed profiles vigorously barbecued. Tom flew to Brazil and tracked down the train robber Ronnie Biggs (whom, inevitably, he both liked and rather admired). He puffed his way across the Alps pointing his microphone at the charity-walking Ian Botham and his elephant. The health minister Edwina Currie once advised him that his fondness for nicotine might lower his sperm count.

The Observer hired Tom to write its Pendennis column in the mid-90s – witty and bone-dry conceits from the perspective of a smoke-fugged bar-stool – but in 1997 he developed pneumonia and acute pancreatitis, and spent three months in the intensive care unit of his local hospital in Hammersmith, west London. In his characteristic resigned and shrugging manner, he spent the last 14 years of his life unable to work and living with the after-effects of an illness from which he never fully recovered.

Tom is survived by his wife, Allyce.

• Tom Hibbert, journalist, born 28 May 1952; died 28 August 2011