Kicking off their night at Katsuya Hollywood, the duo chatted away over dinner at a table policed by two bodyguards. Following the meal, the music moguls headed to the Hollywood Roosevelt Hotel, where the night before Jay-Z hosted a private dinner and afterparty, joined by his wife, Beyoncé.
Arriving just after 11:30 p.m., Usher and Jay-Z, who wore shades, settled into a VIP table in the back of the Roosevelt’s club, Teddy’s, to enjoy the weekly jazz night, sponsored by Hennessy. The guys quietly sipped champagne, then made their way out about an hour later, leaving the partying to such other celebs as Drew Barrymore's boyfriend Justin Long.
Earlier in the evening, Jay-Z watched the Yankees-Red Sox game at Parlor, an upscale sports bar, with four other friends and his security team. Noshing on nachos, chicken paninis and onion rings, the guys washed down the grub with a round of Corona Lights.
Reporting by ABBY STERN and MAUREEN HARRINGTON