After building popularity with their appearance in the movie Mulan, singing "True to Your Heart" which had them collaborate with Stevie Wonder, their success broke out in late 1998 with their album 98 Degrees and Rising, which included the hit singles "The Hardest Thing", "I Do (Cherish You)" and "Because of You".

This TV show grouped four former pop singers, Timmons, Bryan Abrams of Color Me Badd, Rich Cronin of LFO and Chris Kirkpatrick of *NSYNC to form a new band called Sureshot.

In 2012, Timmons joined boy bands A1 and Blue in a Southeast Asian world tour and performed both his solo songs and 98 Degrees singles.

In October 2018, Timmons enjoyed one of the most successful ventures of his career, teaming up with CBS Big Brother Legend and IMPACT Wrestling Superstar Mr. PEC-Tacular Jessie Godderz to record the single The Girl Is With Me.

[4] Together with Emmy-nominated choreographer Glenn Douglas Packard and entrepreneur "Money Mike" Foland, Timmons created the "Men of the Strip" revue, a process documented in a 2014 docusoap film of the same name, produced for the E!

[5][6] Timmons describes the film as "like Magic Mike with elements of Sex and the City: the guys' personal lives, they're fighting to be the best at what they can do, but at the end of the day, they're family.

[4] Timmons describes her as the "brainchild behind the rebirth of my career," referring to the Men of the Strip project, and states "[a]nything that happens forward, if it's a successful endeavor, you can be assured that she's behind it.