Milwaukee Bucks (2014–2016) On June 26, 2014, O'Bryant was selected with the 36th overall pick in the
2014 NBA draft by the
Milwaukee Bucks. On July 30, 2014, he signed with the Bucks after averaging 8.2 points in five
Summer League games for the team. On October 9, he suffered a grade III sprain of the medial collateral ligament (MCL) in his right knee. The injury ruled him out of the first 25 games of the season, as he made his debut for the Bucks on December 17. On December 26, he scored a season-high 12 points in a 107–77 win over the
Atlanta Hawks. On November 11, 2015, O'Bryant had a season-best game with 11 points and 9 rebounds in a loss to the
Denver Nuggets. On June 29, 2016, O'Bryant was waived by the Bucks. On September 23, 2016, O'Bryant signed with the
Washington Wizards, but was later waived on October 21 after appearing in four preseason games.
Northern Arizona Suns (2016–2017) On November 11, 2016, O'Bryant was acquired by the
Northern Arizona Suns of the
NBA Development League. He made his debut for the Suns in the team's season opener the following day, recording 18 points and 12 rebounds in a 122–106 win over the
Iowa Energy. On January 16, 2017, he was named NBA Development League Performer of the Week for games played Monday, January 9 through Sunday, January 15.
Denver Nuggets (2017) On January 26, 2017, O'Bryant signed a 10-day contract with the
Denver Nuggets. On February 6, 2017, he signed a second 10-day contract with the Nuggets.
Return to Northern Arizona (2017) O'Bryant returned to the Northern Arizona Suns on February 16 following the expiration of his second 10-day contract. Two days later, he participated in NBA D-League All-Star Game.
Charlotte Hornets (2017–2018) On February 24, 2017, O'Bryant signed a 10-day contract with the
Charlotte Hornets. On March 4, 2017, he scored a career-high 15 points in a 112–102 win over the
Denver Nuggets. Two days later, he signed a second 10-day contract with the Hornets. On March 16, 2017, he signed a multi-year contract with the Hornets. On February 7, 2018, O'Bryant, along with two future second-round draft picks (2020 and 2021), was traded to the
New York Knicks in exchange for
Willy Hernangómez. He was waived by the Knicks the next day.
Maccabi Tel Aviv (2018–2019) On July 31, 2018, O'Bryant signed a one-year deal with the Israeli team
Maccabi Tel Aviv of the
EuroLeague. On December 27, 2018, O'Bryant recorded a career-high 32 points, shooting 5-of-7 from 3-point range, along with five rebounds, three assists and three steals for 44
PIR, leading Maccabi to a 94–92 win over
Olimpia Milano. Two days later, he was named
EuroLeague Round 15 MVP. O'Bryant went on to win the
2019 Israeli League Championship with Maccabi.
Lokomotiv Kuban (2019–2020) On August 14, 2019, O'Bryant signed with
Lokomotiv Kuban of the
VTB United League. He averaged 16.4 points, 5.7 rebounds, and 2.6 assists per game in VTB play. O'Bryant re-signed with the team on July 21, 2020. However, on September 18, he parted ways with the team due to a family issue.
Crvena zvezda (2020–2021) On October 19, 2020, O'Bryant signed with
Crvena Zvezda of the
Adriatic League and the
EuroLeague. On January 27, 2021, he received a 10-day suspension from the club due to a conflict with team head coach
Dejan Radonjić during a game against
Anadolu Efes. On February 21, the Zvezda parted ways with O'Bryant.
Türk Telekom (2021) On February 21, 2021, O'Bryant signed with
Türk Telekom of the
Turkish Basketball Super League, for the remainder of the season. On September 29, 2021, the
Milwaukee Bucks signed O'Bryant to a training camp deal. He did not make the final roster however, and was waived on October 11.
Wonju DB Promy (2021–2022) On November 15, 2021, O'Bryant signed with the
Wonju DB Promy of the
Korean Basketball League to replace
Yante Maten for eight weeks. On January 3, 2022, his contract was expired. On January 5, he re-signed with the Wonju DB Promy for the remainder of the season.
Meralco Bolts (2022) On August 6, 2022, he signed with the
Meralco Bolts of the
Philippine Basketball Association (PBA) as the team's import for the
2022–23 PBA Commissioner's Cup. He was set to be replaced by
Jessie Govan after a 1–5 start to the conference, but O'Bryant stayed with the team when Govan was measured above the conference's 6'10" height limit. He was supposed to play another game on October 30, but the game was postponed due to
Tropical Storm Paeng. On October 31, he was finally replaced by
K. J. McDaniels.
Shanghai Sharks (2022–2023) In October 2022, O'Bryant signed with the
Shanghai Sharks of the
Chinese Basketball Association.
Ibaraki Robots (2023–2024) On November 15, 2023, O'Bryant signed with the
Ibaraki Robots of the
B.League. On April 9, 2024, his contract was terminated.
Gigantes de Carolina (2024) On July 12, 2024, O'Bryant signed with the
Gigantes de Carolina of the
Baloncesto Superior Nacional (BSN).
Uralmash Yekaterinburg (2024–2025) On September 23, 2024, O'Bryant signed with the
Uralmash Yekaterinburg of the
VTB United League. On January 9, 2025, Uralmash Yekaterinburg parted ways with O'Bryant.
Anyang Jung Kwan Jang Red Boosters (2025) On January 13, 2025, O'Bryant signed with the
Anyang Jung Kwan Jang Red Boosters of the
Korean Basketball League (KBL) to replace
Cliff Alexander.
Sagesse SC (basketball) (2025-present) On April 18, 2025, O'Bryant signed with the
Sagesse SC. ==Business career==