Wentworth became identified with the New British Sculpture movement. Wentworth’s interest is the juxtaposition of materials and found elements that do not belong together.[according to whom?] In the work Shower, Wentworth attached a small propeller to an ordinary table creating the impression that the furniture is about to take flight. For an installation at the Lisson Gallery he created a flock of books suspended by wire from the gallery’s ceiling in 1995. For Art and Sacred Places in Winchester Cathedral he created Recall which speculated how the structure of the Cathedral might have been supported during its construction. Wentworth is also interested in the bizarre coincidences of urban life that he documents in photographs. In April 2010, Wentworth participated in a major sculpture exhibition curated by Peter Kardia entitled "From Floor to Sky", alongside artists Roderick Coyne and Alison Wilding.
In 2000, together with Fischli & Weiss and Gabriel Orozco he worked in "Aprendiendo menos" (learning less), curated by Patricia Martín and presented in Centro de la Imagen, Mexico city. Three different perspectives through photography, where the artists are a means to portray street findings within the urban landscape, its surroundings and its objects.
Wentworth has lived for many years in the Kings Cross area of London and in 2002 he realised the project An Area of Outstanding Unnatural Beauty in which for three months he took over a plumbing supply shop in the area converting it into a base for visitors to explore and engage with the area.
In July 2009, he curated the Lisson Gallery's Summer show featuring a large number of works from his personal collection and that of Lisson director Nicholas Logsdail.