Segal has directed the comedic films Naked Gun 33+1⁄3: The Final Insult (1994), Tommy Boy (1995), My Fellow Americans (1996), The Nutty Professor II: The Klumps (2000), Anger Management (2003), 50 First Dates (2004), The Longest Yard (2005), Get Smart (2008), Grudge Match (2013), and My Spy (2020).

[4] Segal made his feature film directorial debut in 1994 with Naked Gun 33 1/3: The Final Insult, starring Leslie Nielsen and George Kennedy.

"[13] Segal directed the comedy film My Fellow Americans (1996), starring Jack Lemmon, James Garner and Lauren Bacall.

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.

[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.

The film starred Steve Carell, Anne Hathaway, Dwayne Johnson, Alan Arkin and Terence Stamp.

[26][27][28][29][30] Segal also directed Grudge Match (2013), which starred Robert De Niro, Sylvester Stallone, Kevin Hart, Alan Arkin, Kim Basinger and Jon Bernthal.