According to Difford, he stole 50p from his mother's purse to put a card in a local sweetshop window advertising for a guitarist to join his band, although he did not have one at the time.

[3] Some of their best-known songs are "Tempted", "Pulling Mussels (From the Shell)", "Black Coffee in Bed", "Cool for Cats", "Up the Junction" and "Annie Get Your Gun".

After the break-up of Squeeze in 1983, Difford continued writing songs for artists such as Jools Holland,[4] Helen Shapiro, Billy Bremner and Elvis Costello.

He was involved with Tilbrook and John Turner in the creation of a musical, Labelled with Love, which was created using the songs of Squeeze.

Squeeze reunited again in 2007, and Difford maintained a concurrent solo career alongside his work with the band.