The Canadian hip-hop star served as the headliner for the second day of the event, but instead of delivering a solo show, he invited a slew of famous friends to give attendees a night to remember.
After an opening set by previously-announced performer Jhene Aiko, former Fugees star Hill was introduced to the stage, much to the crowd's delight, and delivered renditions of Killing Me Softly, Ooh la la la, Ready Or Not and Doo Wop (That Thing).
Drake then took over the show and launched into his back catalogue of songs, with guest appearances from R&B star Trey Songz, rapper J. Cole, singer Partynextdoor, DJ Khaled, Tinashe and Yg.
He also paid tribute to his sick mother, Sandi Graham, by having her brought out onstage in a wheelchair to greet the audience during the 5th Annual OVO Fest.
However, it was Usher who sent fans into a frenzy as he joined Drake in the spotlight and played a string of his popular tracks, including Climax, Lovers and Friends, Confessions Pt. Ii and U Don't Have to Call.
Drake also brought 50 Cent and his G-Unit group up onstage for renditions of Gangsta, I Get Money and In Da Club, before closing his two-and-a-half hour gig with Worst Behaviour and 0 to 100.
Reunited hip-hop duo Outkast had been the main attraction during Sunday's (03Aug14) festivities.