Pickles was born in Halifax in the West Riding of Yorkshire. He moved to Southport, Lancashire, with his family in 1929, and worked with his father as a builder. He joined an amateur dramatic society, and in a local production there met Mabel Cecilia Myerscough (1906–1989), all of whose family had been connected with the stage.

His most significant work was as host of the BBC Radio show Have A Go, which ran from 1946 to 1967 and launched such catchphrases as “How do, how are yer?”, “Are yer courting?”, “What’s on the table, Mabel?” and “Give him the money, Barney”. He appeared in the show with his wife Mabel, whom he had married at Sacred Heart Roman Catholic Church, Ainsdale, Southport on 20 September 1930.

In 1948, a children’s board game entitled Ask Pickles was published by jigsaw puzzle manufacturer Tower Press.

In 1950, he was awarded the OBE for services to broadcasting.

He was the guest castaway on BBC Radio’s Desert Island Discs on 2 January 1953; his chosen book was The Oxford Book of English Verse edited by Arthur Quiller-Couch, and his luxury a yellow waistcoat.

The series attracted a weekly audience of over 20 million and a mailbag of around 5,000 letters. Contestants could earn £1/19s/11d by sharing “their intimate secrets”. In May 1954, he took the show to television with the programme Ask Pickles which ran until 1956. The show was publicized enthusiastically by the BBC:

In 1955, Wilfred Pickles published an anthology of poetry and prose of the “north counties” of England. The book, My North Countrie, featured verses from a range of poets and writers including two Lancashire dialect verses, “A Bird Song Away” and “Th’ Art Lookin’ Sackless”, from the award-winning weaver-poet Nicholas Freeston.

In 1955, he opened the Wilfred Pickles’ School for Spastics at Tixover Grange, Rutland. Also in 1955, he and wife Mabel celebrated their silver wedding anniversary by returning to the Sacred Heart Church in Southport, when they gave money for a statue of Saint Teresa Margaret of the Sacred Heart, which still stands in the church. They recorded an edition of Have a Go from the church hall (now demolished), and later performed a version of the show in the adjacent school for the children.

He was in the play Come Laughing Home by Keith Waterhouse and Willis Hall on BBC Radio 4 in 1970. In 1971, he was the subject of This Is Your Life.

Pickles died in Brighton on 27 March 1978, aged 73, and is buried with his wife Mabel in Southern Cemetery, Manchester.