Segal began his career writing and directing television. In 2002, he created the NBCsitcomHidden Hills (2002–2003). In 1995, he formed his production company, Callahan Filmworks, along with long-time producing partner Michael Ewing.[4]
Segal went on to direct Chris Farley and David Spade in Tommy Boy (1995).[10][11] Though it received mixed reviews at the time of release, and was considered a commercial disappointment,[12]Tommy Boy's reputation has grown over the years and it is considered in some quarters a "now-iconic cult classic."[13]
Segal directed the comedy filmMy Fellow Americans (1996), starring Jack Lemmon, James Garner and Lauren Bacall.[3][4] The film received mixed reviews from critics. It holds a 47% rating on Rotten Tomatoes based on 60 reviews and with an average rating of 5.3/10 and the critical consensus: "It doesn't commit any impeachable offenses, but My Fellow Americans lacks strong regulatory oversight of its toothless political satire and misuse of comedic talent."[14] Co-star Garner was not impressed by Segal, writing in his memoirs that Segal "was a self appointed genius who didn't know his ass from second base and Jack and I both knew it."[15]
Segal next directed the comedy Nutty Professor II: The Klumps (2000), starring Eddie Murphy.[3][4] The film was a substantial commercial success, grossing $42.5 million in its opening weekend, the then-highest opening weekend for an Eddie Murphy film.[16] The film went on to generate a total gross of $166.3 million worldwide.[17] Critically, however, the film did not fare as well: on Rotten Tomatoes, the film has an approval rating of 27% and an average rating of 4.5/10, based on reviews from 89 critics. The site's consensus states that "While Eddie Murphy is still hilarious as the entire Klump family, the movie falls apart because of uneven pacing, a poor script, and skits that rely on being gross rather than funny."[12] On Metacritic, the film has a score of 38 out of 100, a score that indicates generally unfavorable reviews, based on reviews from 34 critics.[18]
Segal directed Adam Sandler for the first time in Anger Management (2003), which also starred Jack Nicholson.[19][20][21] When asked by the BBC who was the most famous person in his contacts book, Segal replied, "I have to say, it's very obvious now, it's Jack Nicholson. I've kept his number on my speed dial just so I can show it to friends. I could call him up out of the blue, but I'm worried he might say 'Pete who?'"[3]
Segal collaborated with Sandler for the third time in The Longest Yard (2005), a remake of the 1974 film of the same name.[2][3] The film has become the second highest grossing sports comedy in history.[4]
When asked in a September 2014 interview by the BBC if he believes in God, Segal replied: "I do. I'm very spiritual and I'm Jewish by faith. I'm not a practising Jew, I'm more of a recreational Jew. I celebrate the holidays and I try to inform my kids about their heritage because I think we all at some point have to defend our heritage and if they get picked on I want them to know why."[3]