Who dated Matt Dillon?
Cameron Diaz dated Matt Dillon from until . The age gap was 8 years, 6 months and 12 days.
Roberta Mastromichele dated Matt Dillon from until . The age gap was 12 years, 3 months and 23 days.
Matt Dillon

Matthew Raymond Dillon (born February 18, 1964) is an American actor. He has received various accolades, including a Screen Actors Guild Award and two Independent Spirit Awards alongside nominations for an Academy Award, a Golden Globe Award, and a Grammy Award.
Dillon made his feature film debut in Over the Edge (1979) and established himself as a teen idol by starring in the films My Bodyguard (1980), Little Darlings (1980), Liar's Moon (1982), The Flamingo Kid (1984) and three of the four S. E. Hinton book adaptations: Tex (1982), Rumble Fish (1983) and The Outsiders (1983). From the late 1980s onward, Dillon achieved further success, starring in Drugstore Cowboy (1989), Singles (1992), The Saint of Fort Washington (1993), To Die For (1995), Beautiful Girls (1996), In & Out (1997), There's Something About Mary (1998), and Wild Things (1998). In a 1991 article, movie critic Roger Ebert referred to him as the best actor within his age group, along with Sean Penn.
In 2002, he made his directing debut with City of Ghosts and has since continued to act in films such as Factotum (2005), You, Me and Dupree (2006), The House That Jack Built (2018), and Asteroid City (2023). For Crash (2004), he won an Independent Spirit Award and was nominated for a Golden Globe Award and the Academy Award for Best Supporting Actor. He had earlier been nominated for the Grammy Award for Best Spoken Word Album for narrating Jack Kerouac's On the Road. On television, he starred in the first season of the FOX television series Wayward Pines (2015), for which he was nominated for a Saturn Award.
Read more...Cameron Diaz

Cameron Michelle Diaz (born August 30, 1972) is an American actress. Prolific in both comedy and drama, her films have grossed over $3 billion in the U.S. box-office. Her output of romantic comedies in the late 1990s and early 2000s established her as a prominent sex symbol and one of Hollywood's most bankable stars, and in 2013 she was named the highest-paid actress over 40. Diaz has received various accolades, including nominations for a British Academy Film Award and four Golden Globe Awards.
Born in San Diego, California, Diaz was raised in Long Beach. While still in high school, she signed a modeling contract with Elite Model Management. She made her film debut at age 21 opposite Jim Carrey in the comedy The Mask (1994). Following a supporting role in the romantic comedy My Best Friend's Wedding (1997), she starred as the titular character in the Farrelly brothers' comedy There's Something About Mary (1998), which brought her increased fame and her first Golden Globe nomination. Her following two projects—the sports drama Any Given Sunday and Spike Jonze's fantasy film Being John Malkovich (both 1999)—earned Diaz recognition as a dramatic actress.
Diaz received praise for her supporting roles in Cameron Crowe's Vanilla Sky (2001) and Martin Scorsese's Gangs of New York (2002) and had greater commercial success in the action comedy Charlie's Angels (2000) and its 2003 sequel, as well as for voicing Princess Fiona in the Shrek franchise since 2001. Her subsequent films include the comedies In Her Shoes (2005), The Holiday (2006), What Happens in Vegas (2008), Knight and Day (2010), The Green Hornet (2011), and Bad Teacher (2011). After starring in three successful comedies in 2014—The Other Woman, Sex Tape and Annie—Diaz retired from acting to focus on her family, but made a return to the profession with the action comedy Back in Action (2025).
Diaz has also written two health books: The Body Book (2013), a New York Times bestseller, and The Longevity Book (2016). Her personal life has drawn media attention throughout the course of her career, mostly regarding her relationships and fashion choices. In 2015, Diaz married Good Charlotte guitarist Benji Madden; they have two children via surrogate.
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