From 2014 to May 2022, he was featured on The Ellen DeGeneres Show as a repeated guest host and he was also a co-executive producer of the program.

[1] He graduated from Lee High School in 2000 and studied dance performance at Southern Union State Community College in Wadley, Alabama, and Chapman University.

[2] In 2003, Boss was a semifinalist on MTV's The Wade Robson Project and a runner-up on the television talent competition Star Search.

[3] He choreographed routines for South Korean pop/R&B singer Seven and helped train other YG Entertainment artists including Big Bang.

[15] He returned to audition again in Season 4 in 2008; he was selected to compete in the Top 20 and finished the competition as runner-up to fellow hip-hop dancer Joshua Allen.

[25] On October 17, 2017, Freeform announced the production of a seven-episode series to be released in the summer of 2018; it was hosted by Boss and Allison Holker.

In November 2017, Freeform added a December 11, 2017, hour-long special, "Disney's Fairy Tale Weddings: Holiday Magic" as a part of its "25 Days of Christmas" event.

[27] On December 10, 2013, Boss and fellow SYTYCD alum Allison Holker married at Nigel Lythgoe's Villa San Juliette Vineyard and Winery in Paso Robles, California.