Josh Strickland, who started performing musical theater in high school at South Carolina’s Charleston County School of the Arts, went on to the national tour of Rent. He appeared on season 2 of Fox TV's American Idol, Star Search, and in March 2007 as himself on All My Children.

He starred as Tarzan in Disney's production of Tarzan on Broadway at the Richard Rodgers Theatre.

The production's run ended after some 14 months and Strickland performed the final show along with the rest of the original cast, minus Shuler Hensley, who had left the production to work on the new Mel Brooks musical Young Frankenstein and was replaced by Rob Evan. The final performance was on July 8, 2007.

In 2009, Strickland became an original cast member of Peepshow in Las Vegas. He has befriended his costar Holly Madison and could be seen regularly in her television reality show Holly's World. He is also a friend of Laura Croft, Miss July 2008 Playboy Playmate as well as stage Actress/Dancer Angel Porrino.

On February 16, 2011, Strickland debuted his first ever solo artist single on iTunes titled "Report to the Floor." The track was co-produced by Grammy Award winning producer Damon Elliott and by Norwegian pop/dance producer Axident. This was closely followed by his second single titled "Last Dance".

As of September 12, 2013, Strickland was cast as one of the lead roles in VEGAS! the Show, performing as Elvis and other iconic artists in the world famous "Vegas themed" musical showing at the Saxe Theater inside Planet Hollywood Resort & Casino's Miracle Mile Shops. Strickland was immediately cast by David Saxe after the closing of Peepshow and subsequently replaced longtime VEGAS! the Show Elvis performer, Lou Gazzara.