From singing and dancing in the Mickey Mouse Club to making boy band history as a member of *NSYNC, to becoming a major Hollywood mogul with a thriving solo music career, starring roles in upcoming films Friends with Benefits and Bad Teacher, his own clothing line, restaurants, and, yes, even his own brand of tequila, listing Justin Timberlake’s many accolades is a seemingly endless task. Seriously—we’re not even going to try. But here are 25 fun facts you may not know about the curly-haired southern boy who brought sexy back and took Hollywood by storm.

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1. He does a full-on dry-humping scene with ex-girlfriend Cameron Diaz for his role in Bad Teacher. (Can you say awkward?) And according to Diaz, he not only did an awesome job but also made her feel totally comfortable. JT gets a gold star in our book for pulling that off with grace.

2. His childhood nickname was Curly. So cute!

3. When he was just a little curly-haired nugget from Tennessee, Justin’s mother entered him in talent contests where he sang country music and danced. At age 10, he was given the honor of singing before a crowd at the Grand Ole Opry.

4. Timberlake was raised Baptist (his grandfather was a Baptist minister), but he now considers himself to be more "spiritual than religious."

5. He’s on Simon Cowell’s s*** list. In a 2004 interview with People Magazine, the American Idol judge described Timberlake as "some white kid who's tried to act black over the last several years.” Six Grammy awards and two Emmy’s later, guess who’s eating their words now?

6. He made boy band history. In March 2000, 'N Sync’s second album, No Strings Attached, sold 2.4 million copies sold in its first week, making it the fastest-selling album of all time. 

7. Speaking of Simon…  Timberlake—along with Chris Isaak, Shania Twain and Elton John—was on American Idol producer Simon Fuller’s short list to replace Cowell on the judge’s panel after he left the show in 2010.

8. And speaking of Elton John… JT played a young Elton John in the music video for John's "This Train Don't Stop There Anymore."

9. Justin and his close friend and business partner, Trace Ayala launched their new clothing line, William Rast, in 2006. The line was inspired by Timberlake’s admiration for his grandfather’s fashion sense—as a tribute to their stylish grandpas, the name “William Rast” is a combination of their grandfathers' names.

10. His hit single, “What Goes Around…/… Comes Back Around,” is said to have been written about Ayala’s break-up with actress Elisha Cuthbert.