Before Justin Timberlake had nine Grammys and a Golden Globe nomination to his name, he was *NSYNC‘s curly-haired heartthrob.
*NSYNC’s ‘No Strings Attached’ Turns 15: What’s the Best Song on the Album?
To commemorate the 15th anniversary of *NSYNC’s sophomore album, No Strings Attached (released March 21, 2000), here’s a look at how JT has transitioned from the stage to the big screen, saying “bye bye bye” to his boy band days and polishing his film resume.
Below are the singer-turned-actor’s most memorable film roles:
1. Inside Llewyn Davis (2013)
Timberlake brought his musical background to the Oscar-nominated film Inside Llewyn Davis, a music drama centered on the life of a struggling folk singer (played by Oscar Isaac). He played the role of fellow musician Jim Berkey and earned a Golden Globe nom for best original song for contributing to the film soundtrack’s hit “Please Mr. Kennedy.”
2. Friends with Benefits (2011)
The romantic comedy starred Timberlake and Mila Kunis as two single friends who begin a casual relationship as hook-up partners and later find themselves developing romantic feelings for each other.
3. The Social Network (2010)
The Mark Zuckerberg biopic saw the singer take on the role of Napster co-founder Sean Parker. In the film, Timberlake’s character coaches Zuckerberg on how to build a successful business model and advises him to drop the word “the” from Facebook’s would-have-been site name, “The Facebook.”
4. Runner Runner (2013)
Timberlake starred as a poor Princeton grad student who uses online gambling to pay off his tuition in 2013’s Runner Runner, which also featured Ben Affleck and Gemma Arterton in leading roles.
5. Bad Teacher (2011)
The singer starred opposite former flame Cameron Diaz and Jason Segel in the 2011 comedy film, which saw him in the role of dorky and innocent substitute teacher Scott Delacorte.
6. In Time (2011)
In the sci-fi thriller, Timberlake and Amanda Seyfried fight for immortal youth in a dystopian world where everyone stops aging at 25 and must contend for every last second of their lives. Olivia Wilde, Cillian Murphy and Matt Bomer co-star.
7. Alpha Dog (2006)
For one of his earliest film roles, the former *NSYNC member portrayed one of the henchmen of Johnny Truelove, a character based off of the real-life infamous drug dealer Jesse James Hollywood, in 2006’s Alpha Dog. The biopic also starred Bruce Willis, Emile Hirsch, Sharon Stone and Ben Foster.
This article originally appeared in THR.com.