Lord Cowdray is the son of Weetman Pearson, 3rd Viscount Cowdray (1910–1995). His great-grandfather, Weetman Dickinson Pearson, 1st Viscount Cowdray (1856–1927), was created Viscount Cowdray in 1917. His mother, Lady Anne Pamela Bridgeman (1913–2009) was the daughter of Orlando Bridgeman, 5th Earl of Bradford (1873–1957). He grew up on the 16,500-acres family estate in West Sussex.
He attended Gordonstoun School, a boarding school in Elgin, Moray, Scotland.
He was, following school, in the British Army for two years.
In the late 1960s, he started a career as a film producer, running Cupid Productions, a film production company. He produced Sympathy for the Devil, a film starring The Rolling Stones and directed by Jean-Luc Godard, and Vanishing Point in 1971.
He was a director of Theo Fennell PLC.
In 1995 he took over the family estate, a 16,500-acre estate in West Sussex. He and his wife have tried to make it an economically viable estate through means of sustainable farming. They renovated the main house on the estate to become a venue for private hire and weddings. The estate, which employs 150 people, also has many businesses, including a farm shop, cafe, golf, shooting grounds, fishing and therapy rooms for hire.
The estate is most well known for its polo grounds, hosting one of Britain's most prestigious polo events: the Cowdray Park Gold Cup.
In 1970, he had a child out of wedlock, Sebastian William Orlando Pearson, with Barbara Page. In 1977 he was married Ellen Erhardt. They were divorced in 1984. In 1985, he was listed in Debrett's Peerage as a resident of Le Schuylkill, a high-rise building in Monaco.
In 1987, he married Marina Rose Cordle, daughter of John Cordle, a Conservative Member of Parliament from 1959 to 1977. They have five children:Eliza Anne Venetia Pearson (born 31 May 1988), has two daughters (b. 2014 and 2016) with her partner Leif Christian Kvaal,
Emily Jane Marina Pearson (born 13 December 1989),
Catrina Sophie Lavinia Pearson (born 13 March 1991),
Peregrine John Dickinson Pearson (born 27 October 1994)
Montague Orlando William Pearson (born 17 May 1997).
Lord Cowdray has served on the board of trustees of the Tibet House Trust for 20 years. and donates to the school project The Drukpa Kargyu Trust. He is a patron of the local primary school, church, young farmers club and sports teams.Last of the Long-haired Boys (1968)
Sympathy for the Devil (1968)
The Legend of Spider Forest (1971)
Vanishing Point (1971)