Born in Cleveland, Ohio and raised in Farmington Hills, Michigan, Benson attended Detroit Country Day School in Beverly Hills, Michigan. On the Detroit Country Day basketball team, Benson averaged only 6.9 points and 4.5 rebounds per game as a senior. Benson initially committed to Fairfield, but changed his mind after a coaching change and committed to Oakland after they offered him a scholarship.
After redshirting his first year at Oakland, Benson became a starter for the 2007–08 season. Benson started 20 of the team's 29 games and averaged 5.2 points and 3.5 rebounds. He finished the season with 40 blocks—one shy of Oakland's single-season record. However, he was benched prior to the conference tournament because OU's head coach, Greg Kampe, felt Benson was not playing good enough defense.
At the conclusion of his redshirt junior season, Benson received the Lou Henson Award, given to the "mid-major player of the year". Benson was also named the Summit League Player of the Year. Benson declared himself eligible for the 2010 NBA Draft, but withdrew himself after he was unable to work out with NBA teams due to an injured right thumb.
Benson earned a Bachelor of Integrative Studies degree with a minor in art history from Oakland in August 2010, prior to his redshirt senior season. During his senior season in 2010–11, Benson enrolled in master's-level architecture courses in Oakland. In basketball, he set the Summit League's record for career blocks. He broke the record of 317, set by Keith Closs of Central Connecticut State University from 1994–96. Benson was named the Summit League's Player of the Year for the second consecutive season in 2011.
After being projected as a late-second round pick, Benson was selected with the 18th pick of the second round (48th overall) by the Atlanta Hawks. Benson is the first player ever from Oakland University selected in the NBA Draft. In August 2011 he signed a one-year contract with Dinamo Basket Sassari in Italy's Serie A League, which included an opt-out clause upon the conclusion of the 2011 NBA lockout, but he left the team in October 2011.
Once the lockout ended, Benson played in the Hawks' two preseason games and was waived before the beginning of the regular season.
On January 26, 2012, the Sioux Falls Skyforce acquired Benson out of the D-League player pool. On March 24, he signed a 10-day contract with the Golden State Warriors. Benson appeared in only three regular-season games with the Warriors, missing his only shot attempt, and grabbing three rebounds.
In September 2012, Benson joined the Atlanta Hawks after playing with their summer league team. He was waived by the team on October 11, 2012.
On November 3, 2012, Benson was re-acquired by the Sioux Falls Skyforce. However, on November 5, the Skyforce traded him to the Erie BayHawks for Mike Davis. Benson was bought out by the Talk 'N Text Tropang Texters of Manila, Philippines.
The Talk 'N Text Tropang Texters selected Benson as an import for the 2013 Philippine Basketball Association's Commissioner's Cup. He was replaced midseason by Donnell Harvey. In March 2013, he returned to the BayHawks.
In July 2013, Benson played for the Brooklyn Nets and Charlotte Bobcats during the 2013 NBA Summer League. Later that year, he joined Tsmoki-Minsk of Belarus for the 2013–14 season.
In July 2014, Benson joined the Los Angeles Clippers for the 2014 NBA Summer League. On August 1, 2014, Benson signed with Banvit in Turkey. On September 20, 2014, he parted ways with Banvit. On October 31, 2014, he signed with Neptūnas of Lithuania for the rest of the 2014–15 season. On February 27, 2015, he left Neptūnas and signed with BC Kalev/Cramo of Estonia.
In July 2015, Benson joined the Orlando Magic for the 2015 NBA Summer League. On August 25, 2015, he signed with the Miami Heat. However, he was later waived by the Heat on October 24 after appearing in five preseason games. On November 2, he was reacquired by the Sioux Falls Skyforce as an affiliate player of the Heat. After averaging 13.4 points and 6.9 rebounds in 27 games for the Skyforce, he was named in the East All-Star team for the 2016 NBA D-League All-Star Game on February 5, as a replacement for the injured Jordan Mickey. He helped the Skyforce finish with a D-League-best 40–10 record in 2015–16, and went on to help the team win the league championship with a 2–1 Finals series win over the Los Angeles D-Fenders.
On September 23, 2016, Benson signed with the Miami Heat. However, he was later waived by the Heat on October 18 after appearing in three preseason games. On November 1, 2016, he was reacquired by the Sioux Falls Skyforce.
Benson's mother Janice Ellen Hale is a professor of early childhood education at Wayne State University and founding director of the Institute for the Study of the African American Child at Wayne State.