Justin Timberlake made the leap from boy band singer to Sinatra-style musical alpha male in the early 2000s. He was first among equals in the 1990s teen band *NSYNC. Timberlake sang lead on many tracks of the band's multi-platinum albums, including *NSYNC (1998), No Strings Attached (2000) and Celebrity (2001), and his charisma and good looks made him a favorite with female fans. (His popularity was helped by his on-again, off-again romance with pop songstress Britney Spears.) Timberlake went solo with the 2002 album Justified, which established him as a hunky urban leading man. Justified won Grammy Awards for best pop vocal album and best male pop vocal performance for the single "Cry Me A River." His second album, FutureSex/LoveSounds, came out in 2006 and had a stronger R&B tilt; it included the hit single "SexyBack" and established him as a fashion plate as well as a singer. That same year he co-starred in two feature films, Black Snake Moan (with Christina Ricci) and Alpha Dog (with Bruce Willis and Sharon Stone). Meanwhile he remained a tabloid favorite thanks to his romances with actresses Cameron Diaz (2003-06) and Jessica Biel (starting in 2007). Timberlake launched his own label, Tennman Records, in 2008 and continued a steady stream of concert performances, TV appearances, and album guest shots.

Extra credit: Timberlake and fellow *NSYNC member J.C. Chasez were regular cast members (along with Britney Spears and Christina Aguilera) on the 1990s TV revival of The Mickey Mouse Club... Timberlake found himself at the center of a public rhubarb in 2004, after he ripped off a portion of fellow singer Janet Jackson's costume, exposing her breast, during a halftime performance at the Super Bowl. He later apologized for the incident, attributing it to a "wardrobe malfunction"... He had a role as a wife-stealing French-Canadian hockey goaltender in the infamous 2008 film flop The Love Guru.