[5] In January 2004, Ross' father was killed at age 66 in a mountain climbing accident near Cape Town.

Ross received rave reviews for his role as troubled teenager Amare McCarter in the HBO television film Life Support, starring alongside Queen Latifah and his real-life half-sister Tracee Ellis Ross, who portrayed his elder sister in the film.

In 2010, Ross joined the cast of The CW's teen drama series 90210 in its third season, portraying Liam Court's (Matt Lanter) half-brother and the love interest to Annie Wilson, played by Shenae Grimes.

[8] That same year, he appeared in Case 219, and the critically acclaimed film festival winner Mooz-lum, also starring Danny Glover and Nia Long.

He then starred in the comedy-drama The Family Tree (2011) and co-starred alongside Brittany Snow in the thriller 96 Minutes, which was released April 28, 2012, in select theaters.

In 2012, Ross had a supporting role in the Jay and Mark Duplass-directed comedy-drama Jeff, Who Lives at Home.

[10] Also in 2014, Ross portrayed the role of Messalla in The Hunger Games: Mockingjay – Part 1, released on November 21.

[12] Beginning in 2017, Ross had a major role as Angel Rivera in the second and third seasons of Fox's drama series Star.

Ross became engaged to singer-songwriter Ashlee Simpson in January 2014, and the two were married that year on August 30 at his mother's estate in Connecticut.