The lineup of hip-hop legends included KRS-One, Slick Rick, Remy Ma, Busy Bee, CL Smooth, DJ Hollywood, DJ Jazzy Joyce, DJ Kevie Kev, Fantastic Five, Furious 5 featuring Grandmaster Melle Mel and Scorpio, Grand Wizard Theodore, Joeski Love, Kid Capri, Nice & Smooth, PopMaster Fabel, Soul Sonic Force, T La Rock, Ultra Magnetic MC's.
More concerts are scheduled Tuesday at Midland Beach on Staten Island, Thursday at the Brooklyn Army Terminal in Brooklyn, and Friday at Forest Hills Stadium in Queens, CBS2's Ali Bauman reported.
Then on Saturday, there will be a mega performance on the Great Lawn at Central Park.
All of the artists taking part in the outdoor concerts have New York roots.
Homecoming Week is designed as a celebration of the city's recovery, but health officials say for a full recovery, more people need to be vaccinated.
New Yorkers in attendance on Monday night said they were enjoying the big party in the boogie down.
"Outside under the stars in the city. I love it, couldn't ask for more," said Dawn Wood of Manhattan.
"It's so refreshing. I really miss going to concerts," said Mariah Smith of Queens.
"This is bringing people together," added Leroy Webber of the Bronx.
The concert lineup is a sign of the city's resilience, after it went from being the epicenter of the pandemic to re-emerging as the epicenter of culture once again.
"This is the best thing that they could've done because people haven't been able to get out, so it's great," Parkchester's Andra Vilson said.
"New York needs this," added Bernadette Clemons of Jamaica, Queens.
The live outdoor shows are also meant to attract business back to mom and pop shops in each borough to help with the Big Apple's full recovery.
"To get there we've got to defeat the Delta variant," Mayor Bill de Blasio said.
Officials say the key is vaccinations. All health care workers in New York state will be required to have at least one dose by Sept. 27.
And starting Tuesday in the city, both workers and patrons of gyms, restaurants and indoor entertainment venues, like theaters and museums, will be required to show proof of at least one vaccine shot with the city's NYC COVID Safe app, the state's Excelsior Pass or a paper vaccination card.
READ MORE: NYC's Proof Of Vaccination Policy
"The new regulation is heaven for us, because now it's not our idea. We respect the regulations of the city," said Fernando Salomone, BeFitNYC owner.
City Hall will spend the next few weeks educating businesses on the requirements and offer training on how to deal with customers who refuse, and then enforcement starts Sept. 13.
Those who are caught not complying will face a $1,000 fine for their first offense, $2,000 for a second offense, and $5,000 for a third.
The city is leading by example, requiring everyone 12 and over at the Homecoming Week concerts to show proof of at least one vaccine dose.
"Keeping everybody safe at the same time," Webber said.
In addition to concerts, there will also be film screenings in all five boroughs.
Tickets to the shows are free and can be found at NYC.gov/HomecomingWeek.
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