Long has had a number of high profile celebrity relationships, dating Drew Barrymore from 2007 to 2008 (the pair later starred in He's Just Not That Into You and Going the Distance together) and Amanda Seyfried from 2013 to 2015. In 2018, Long enjoyed a two-episode stint on The Conners as Neil, a potential love interest for Darlene (Sara Gilbert), and he was also cast as a fussy lawyer in Kevin Smith's hotly anticipated 2019 sequel, Jay and Silent Bob Reboot. He also loaned his voice to the Alvin and the Chipmunks film trilogy series as the titular troublemaking rodent. He later had memorable parts in Zack and Miri Make a Porno and Funny People. He moved into action territory with Live Free or Die Hard and went back to horror with Drag Me to Hell. From there, he starred in a number of comedies including The Break-Up and Accepted.
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