Winterbottom did a good job helming installments of TV series, including the two-hour premiere of "Cracker" subtitled "The Mad Woman in the Attic" (Granada, 1993; aired in the US on A&E in 1994), and he also helmed the "Death at the Bar" episode for "The Inspector Alleyn Mysteries" (BBC/PBS, 1995). A breakthrough, though, came with his four-part serial, "Family" (BBC, 1994), an acclaimed study of a dysfunctional Irish working-class family written by Roddy Doyle. Some of Winterbottom's work, including an edited-down version of "Family", had played well at film festivals, but it was not until "Butterfly Kiss" (1995) that he made a film directly for feature release. An odd, often engaging and touching tale which revisits the road film genre in its mix of lesbian love and serial murder, it showed Winterbottom's promising talent for actors as well as his penchant for emotional extremes and flashy shock cuts. His stylish, personal and often socially committed touch also showed in his study of a multiple sclerosis victim, "Go Now" (1995).
A number of qualities which his work had manifested were present in his most ambitious undertaking to date, an adaptation of Thomas Hardy's bleak, difficult but rewarding novel "Jude the Obscure". Retitled "Jude" (1996), Winterbottom's film suggested his ongoing debts to Bergman and to Francois Truffaut, as well as his admirably restless if not always successful attempts at distancing effects. Very handsomely shot and produced, and featuring a mature star performance by Kate Winslet, the film was generally well-received, despite the challenges of its length, austerity and mixed ambitions. Winterbottom also set himself challenges anew with his present-day historical study of potent emotional bonds formed that are explored in "Welcome to Sarajevo" (1997). Debuting in competition at the Cannes Film Festival, the film received praise for its restrained, yet disturbing examination of the effects of war. In 2002, Winterbottom directed the musical drama "24 Hour Party People," a feature that intertwines music, sex, drugs and a lot of partying people.