He played a soldier in Dear John, a film based on the popular Nicholas Sparks bestseller.
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He was initially reluctant to take the role as he feared the movie would glorify war however, he overcame his reluctance after reading the script. Joe: The Rise of Cobra, Paramount Pictures' live-action film based on the popular Hasbro action figures. The same year, Tatum starred as Duke in G.I. Tatum next appeared in writer/director/producer Michael Mann's 2009 crime drama Public Enemies, playing the 1930s American gangster Pretty Boy Floyd. Tatum starred as Sean McArthur, a young man who scrapes up a living scalping tickets in New York City. Tatum and Dito Montiel, who worked together on A Guide to Recognizing Your Saints, reteamed on the action drama Fighting for Rogue Pictures. Tatum played in the short film The Trap, directed by Rita Wilson. In 2008, Tatum co-starred in director Kimberly Peirce's film Stop-Loss, about soldiers returning home from the Iraq War, and in director Stuart Townsend's film Battle in Seattle, about the 1999 protest of the World Trade Organization meeting in Seattle. Although it was widely panned, it has earned $115 million worldwide.
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Later that year, Tatum starred opposite his former wife Jenna Dewan in Step Up, which was his breakout role. In 2006, Tatum starred in She's The Man opposite Amanda Bynes, which was named "the greatest Shakespeare adaptation since '10 Things I Hate About You'" by Business Insider. Tatum signed with Ford Models in New York City. He was picked as one of Tear Sheet magazine's "50 Most Beautiful Faces" of October 2001. He was cast by Al David for Vogue magazine and soon after appeared in campaigns for Abercrombie & Fitch, Nautica, Dolce & Gabbana, American Eagle Outfitters, and Emporio Armani. He subsequently signed with (Page Parkes Modeling Agency), a modeling agency in Miami. He soon moved into television commercials, landing national spots for Mountain Dew and Pepsi in 2002. His experience in the fashion industry began as a model working for noted clients such as Armani and Abercrombie & Fitch. In 2000, Tatum was first cast as a dancer in Ricky Martin's " She Bangs" music video, after an audition in Orlando, Florida he was paid $400 for the job. Tatum moved to Miami, where he was discovered by a model talent scout. In 2010, he told an Australian newspaper that he wanted to make a movie about his experiences as a stripper.
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Us Weekly reported that around this time Tatum left his job as a roofer and began working as a stripper at a local nightclub, under the name "Chan Crawford". He returned home and started working odd jobs. He later attended Glenville State College in Glenville, West Virginia on a football scholarship, but dropped out. His parents wanted more effort and gave him the option of selecting a private high school or attending a military school he chose Tampa Catholic High School, where he graduated in 1998 and was voted most athletic. Tatum spent most of his teenage years in the Tampa area, and initially attended Gaither High School. Growing up, Tatum played football, soccer, track, and baseball he has said that "girls were always biggest distraction in school." As a child, he practiced wuzuquan kung fu. Tatum has discussed having dealt with attention deficit disorder (ADD) and dyslexia while growing up, which affected his ability to do well in school. He grew up in the bayous near the Pascagoula River, where he lived in a rural setting. His family moved to the Pascagoula, Mississippi area when he was six. Tatum was born on April 26, 1980, in Cullman, Alabama, to Kay Tatum (née Faust), an airline worker, and Glenn Tatum, a construction worker.