Kicking things off Friday at the Wells Fargo Center was Dave Chappelle and The Roots.
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"That's our favorite comedian of all time, we love him so much. I could not miss this opportunity for anything," said Jenel Boone-Harris of West Oak Lane.
Dave Chappelle fans lined up to get inside the Wells Fargo Center Friday night.
SEE ALSO: The Roots Picnic Weekend | What you need to know about the show, tickets, prohibited items
"We're expecting all the raw stuff. We want down and dirty, tell us everything," Boone-Harris said.
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It's not just Dave Chappelle people are excited to see this weekend.
Kunda Chikwanba traveled 20 hours all the way from South Africa to Philadelphia.
"My brother decided to bless me with a wonderful experience at the Roots Picnic this whole weekend Friday to Monday. We're gonna start it off here tonight with Dave Chappelle, one of the greatest of all times," explained Chikwamba.
On Saturday and Sunday, the Roots Picnic will be held at the Mann Center with Philadelphia's own Eve and Lil Uzi Vert. Eight-time Grammy Award winner Usher is also part of the lineup alongside Ms. Lauryn Hill and The Roots.
To learn more about the full weekend lineup and more, click here.
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Ed Sheeran is also in Philadelphia this weekend. He played at The Met Friday night and there will be another show on Saturday at Lincoln Financial Field.
"I just love that he does the smaller venues. This was a last-minute thing he decided to do. This weekend is our third and fourth Ed Sheeran concert," said sisters Laura Blessington and Julianna Callahan.
To top things off beginning this weekend, Pride Month activities are now in full swing, including the unveiling of the largest pride flag in Philadelphia. It's likely one of the top five largest pride flags in the country.
"Unique, one of a kind, no better place, or city, or state to have a flag like this," said Jen Nagle, executive vice president of Philadelphia Visitor Center Corporation.
But the 200-foot-long banner is more than just a flag.
"It's also really how we see our community. It's big, it's vibrant," said Tyrell Brown, the executive director of the nonprofit organization Galaei.
SEE ALSO: FYI Philly celebrates PRIDE month around Philadelphia area