Jerritt Clark/WireImageJay Z may have 99 problems, but putting on an epic boxing match ain't one of them.
Just hours after signing super middleweight champ Andre Ward to his Roc Nation sports empire, the world-famous rapper headed to Madison Square Garden to witness his first ever boxing show as a promoter.
Rihanna, Jake Gyllenhaal, Rosie Perez, Fabolous and Victor Cruz were just some of the famous faces who sat ringside to support Beyoncé's hubby.
"Jake and Rihanna were talking and laughing during part of the matches," an eyewitness told E! News. "It was cute. He was explaining what was going on to her and she seemed very interested in the fight."
Another source added, "Jake knew all the boxers at the event and said hello to everyone. Rihanna was also cheering during the rounds."
Keeping it casual with a white tank-top, denim jeans and a matching jacket, RiRi later congratulated Jay Z on his big night.
"big bro. jigga," she wrote on Instagram while posing with her close friend. "congrats to our champ tonight #Dusty #RocNationBoxingCard."
After a night of epic matchups, RiRi and Gyllenhaal kept the celebrations going as they traveled to the 40/40 club in New York City.
Joined by Jay Z and Fabolous, the group arrived around 1 a.m. to celebrate Angie Martinez's birthday.
"They all hung out in the owner's lounge," a source told E! News exclusively. "Jay was overheard telling friends how happy he was with the night and that he's excited for the next match."
Pretty soon, Jay Z will be running this boxing town too.
—Reporting by Jennifer Cooper and Sara Kitnick