[1] Tolleson had a career .425 batting average and 18 home runs at Paul M. Dorman High School in Roebuck, South Carolina.

[3][4] He was selected by the Minnesota Twins in the fifth round of the 2005 Major League Baseball Draft out of the University of South Carolina.

[7] In 2009, with the New Britain Rock Cats and Rochester Red Wings, Tolleson played all three outfield positions, second, short and third.

[11] On November 13, 2012, Tolleson signed a minor league deal with the Chicago White Sox with an invitation to spring training.

On December 17, 2013, Tolleson signed a minor league deal with the Toronto Blue Jays that included an invitation to spring training.

[16] Tolleson hit his first home run as a Blue Jay on May 23, helping the team to a 3–2 win over the Oakland Athletics.

[17] He played in 109 games for the Blue Jays in 2014, mostly as a pinch hitter and late-innings replacement, and hit .253 with 3 home runs and 16 RBI.

[21] On May 7, Tolleson signed a new minor league contract with the Blue Jays, allowing him to bypass a 10-day waiting period before he could be recalled to Toronto.

[25] On November 23, 2015, Tolleson signed a minor league contract with the Baltimore Orioles that included an invitation to spring training.