Stephens started his footballing career at Division 3 (now EFL League Two) side Leyton Orient as a trainee in 2001. He made his first of 4 league appearances for the club, all coming away from home, in a 3–2 defeat away to York City F.C. on 9 November 2002, a game in which he received a booking. His second appearance was on 18 March 2003 in a 3–1 defeat at A.F.C. Bournemouth, in which he was substituted in the 89th minute for Gabriel Zakuani. His final appearance in the 2002–03 Football League Third Division season was in a 1–0 defeat at Southend United F.C. on 22 March 2003, coming on as a substitute in the 65th minute for Simon Downer.

His final league appearance for the club would be in the 2003–04 Football League Third Division season when he came on as an 82nd minute substitute for Matt Joseph in a 1–1 draw at Mansfield Town F.C. on 16 August 2003. Stephens was then loaned out to Billericay Town F.C. in the Isthmian Premier Division, in the 7th tier of the English football league system for one month, after impressing in a pre-season friendly between Orient and Billericay.

During December 2019, Stephens also starred in the Come Dine with Me Christmas special in a bid to win £1,000 for charity over a week of competitive cooking and hosting. Also in December 2019, Stephens appeared on comedy, music and talk show The Big Narstie Show with friend Big Narstie and comedian Mo Gilligan where they discuss his content and upcoming projects.