Saturday Night Live's Jay Pharoah Reveals the Secret to Asking for an Impromptu Impression (Hint: Wait Until He's Finished Chewing!)
04/12/2016 AT 12:25 PM EDT
Speaking about people who approach him on the street, Saturday Night Live's master impersonator told PEOPLE Monday at the 9th Annual Night of Opportunity Gala at Cipriani Wall Street: "Don't stop doing it. Just look at the surroundings."
He continued, "Like, if I'm trying to enjoy my meal and I'm with my family, don't run up and be like 'Oh, snap, can we get some Denzel [Washington]?' No, you can't get Denzel because my my mouth's full! So, just the appropriate time. I'm the nicest guy ever. I don't care, I can do impressions, just be aware of your surroundings."
The Opportunity Network, which helps underprivileged teens get into (and pay for) college and launch successful careers, honored Pharoah along with director and producer Antoine Fuqua and founder of VICE Media Shane Smith. (Also in attendance: Ethan Hawke and Harvey Weinstein).
The comedian says until he pursued his dream with the help of sacrifices by his family, he was a "fat kid" who worked at Burlington Coat Factory.
Pharoah, known for nailing impressions of such stars as Kevin Hart, Eddie Murphy and Chris Rock on live TV, is not always as confident as he seems.
His impression of President Barack Obama in the presence of the man himself was "the most petrifying experience," Pharoah, 28, told PEOPLE recently – although at the event Weinstein recalled that he "killed" his Presidential performance, impressing everyone in the room.
As for his run-in with Jay-Z, Pharoah says he didn't realize Jay was standing right behind him when he dove into his hilarious mimic.
In between honorees' speeches, two students who have benefited from OppNet's intensive program spoke eloquently about their experiences: Harvard-bound freshman Ethan Ambrose, who earned an internship working at a pediatrician's office after joining OppNet after helping his own mother complete her college education by babysitting his infant sister, and Kelly Tran, who's deciding between Swarthmore, Vassar, Franklin & Marshall and Tufts and was her Vietnamese-immigrant parents' English translator from age 8.
The current James Bond, Daniel Craig, and his Oscar-winning bride Rachel Weisz also made a rare show of public togetherness to receive OppNet's 2014 award.