The Next Jay-Z Might Be Singing on Philly’s Sidewalks

Should the city encourage street performers?

The Made in America concert went down this past weekend, and was by all accounts a rousing success. It’s great that Shawn Carter (aka Jay-Z) was able to put together something that cool in Philly. And it’s even more remarkable when you remember that Jay-Z began his music career as a street hustler, selling tapes out of his trunk, and that Roc-a-Fella Records was started by Carter and two friends because nobody would sign Carter to a record deal.

Anthony Riley (left) and Sean Mitchell Caldwell a.k.a. "Infitain"

Fast forward over 15 years, and that hustler spirit (along with loads of talent) has turned Jay-Z into one of the most popular entertainers on the planet. And if you walk around Philly, you’ll meet guys with that kind of talent, that same level of drive and work ethic, and that same gritty hustle—still trying to catch their big break.

If you’ve spent any time in Center City in the last five years, you’ve probably seen both Anthony Riley and Sean Mitchell Caldwell, better known as Infitain. Riley is an old-school R&B crooner, well known locally for his incredible voice* and his arrest in Rittenhouse Park in 2007 for breaking a noise violation by singing. For the past seven years, Infitain has stood at the corner of Broad and Chestnut, smoothly talking people into buying mixtapes of various artists of numerous genres, from hip-hop to jazz to rock, he has worked with over the years, though he recently got shut down at that spot. Riley is handsome, eloquent and thoughtful. Infitain, who bears a slight physical resemblance to Chris Rock, talks fast and covers a lot of ground quickly, but his words are so heartfelt and optimistic that unlike most pitchmen his somewhat frantic style is endearing. I talked to them both about their beginnings in music, what they love about being a street performer in Philly, and what the city needs to do to encourage more “hustlers.”

How did you guys get started as a street performer (Riley) and salesman (Infitain)?
Riley: I was 19, my mother had (recently) passed, and I was kind of sitting around the house and a little depressed. And my father said to me, “There are guys singing down at Suburban Station.” So I started going down there and singing a capella, just to get out of the house. And it just grew into what it is today.

Infitain: My junior year in high school was when Infitainment (his production company) was birthed. I wanted to be that next rap mogul for music. I was doing this on the weekends, and I was making more money selling CDs than I was making in a regular day’s work. I started to take it seriously. I got a business license. I incorporated a publishing company with ASCAP so I can publish music. And I was selling CDs at Broad and Chestnut for seven years until we had that whole L&I situation.

What was the L&I situation? Why did the city come after you?
Infitain: It wasn’t the city. It was one guy, I can’t blame him. I’m out to do my job, and I can’t blame a guy for doing his job. And it’s taught me, “You want to be able to build on solid ground.” When someone can say, “You can’t be here no more” and all of it can crumble, then the ground you were building on wasn’t all that solid. You want to have something untouchable.

What’s the toughest part about being a street performer in Philadelphia?
Infitain: The no’s, man. The no’s. And I wish the city had more vision about what to do with all of this art and culture here. The right visionary can look at this and see a gold mine. But people feel like they gotta leave, because we’re not smart enough to keep some of this great talent here in the city and benefit from it.

Riley: Philadelphia isn’t really a street performing town per se. It’s more lucrative and more accepted in other cities. Philly isn’t a city built for street performances. Maybe if we had a designated area to perform it would be different. There’s other cities where you can get permits and stuff. There’s nowhere to get permits in Philly for street performances.

They’ll [cops or L&I] be like, “Let me see your permits.” And I’m like, “There’s nowhere to get a permit.” It’s been like this hilarious dialogue that I’ve had with the cops for the past five years.

And everything down here is residential. So the problem isn’t so much the police saying, “You can’t perform on the street.” I think it’s more so that you have people who live right next to where you’re performing.

What can Philly do to be more street performer friendly?
Riley: I think the city needs to care more about street performers. If you go to other cities, the tourists love street performers. But if you look on the top 10 lists of street performer cities, I don’t think Philly even places. It’s not something we support, whereas L.A., New York, New Orleans, Miami, it’s a part of the culture as opposed to something that’s tolerated. Here it’s like, “We’ll tolerate you, but don’t be too fucking loud.”

What’s the best thing about being a street salesman/performer in Philadelphia?
Infitain: I was able to survive, man, I was able to grow and live. I bought a house off of this. And it was strictly off the courtesy of the people. It’s one thing to say I was working hard, but if people didn’t support me, I wouldn’t have been able to do what I did. So I’m really a collective of the energy of Philadelphia. People say there’s no love here, no support here, but I’m a testament (that there is). You just gotta be genuine and you gotta be true. We’re an honest city. We appreciate the truth. I think we can see when something is crap. But when something is real, we can feel that vibe too.

Riley: People in Philly are brutally honest. If you suck, people will tell you about it. But if you’re really good, you’ll get this love that’s just crazy.

What’s next?
Infitain: I want to take the hustle to the corporations. I want to get out of survival mode. I want to do more music publishing. You need music. Where will this music come from? I want some of it to come from the artists I represent.

Riley: I’m going to L.A. The plan is to be there by the end of the year. It’s going to be a combination of street performing, hooking up with entertainment companies, acting, everything. Hopefully get some cruise ship work. Whatever comes. A lot of times you have to go somewhere else to seek opportunities. I’ve lived in Philadelphia my whole life. You can’t say shit about Philly to me. But at the end of the day, there is a ceiling. But the thing I appreciate about Philadelphia is, there’s no hate there. It’s like, “Go, go do it. But don’t forget about us.”

*If you want to have your day made, check out this video I happened to take of Riley and two of his, uh, backup dancers a couple of years ago on Broad Street. Amazing.