When I meet Joe Killian at Central Park’s Rumsey Playfield — the outdoor concert venue that SummerStage has called home since 1990 — it’s a gorgeous summer morning in New York City. After unceremoniously tripping up a staircase, I make a comment about the weather to that effect. Killian gently corrects me: it’s not a “gorgeous” day, it’s a “perfect” day.

Killian would know the difference. As the founder of SummerStage, the summer concert series in New York City that began with a free Sun Ra Arkestra concert in 1986 and has expanded to host free shows across all five boroughs over the next four decades, Killian has seen perfect days, nightmare days and nightmare days that, with the benefit of hindsight, are perfect fodder for great concert stories.

SummerStage has witnessed, and been part of, Central Park’s transformation from the wasteland seen in films like The Warriors (1979) and Cruising (1980) to a tourist- and family-friendly green space. In 1993, after Killian steered the series through its early lean years, the City Parks Foundation officially took over management of SummerStage, after which Killian turned his attention to another iconic NYC location, Radio City Music Hall, and founded Killian + Company (which involved him in a variety of other endeavors, including the bizarre but delightful Duran Duran concert David Lynch filmed for American Express in 2011) and became an Emmy winner.

The musical legends who have appeared at SummerStage are too numerous to rattle off, but for a quick attempt: James Brown, Stevie Wonder, Joan Baez, Celia Cruz, David Byrne, Public Enemy, Patti Smith, The Killers, Mavis Staples, Chaka Khan, Beck, Yoko Ono and more. This year, Angélique Kidjo, Laurie Anderson, De La Soul, Spoon, Black Country, Horsegirl, returning performer Mavis Staples and more are part of the series.

At this point, SummerStage is part of the city’s live music fabric, an NYC institution. But if you had told that to a young Joe Killian in the late ‘80s when he was scraping pennies to get performers onto the stage at Central Park’s Naumburg Bandshell, he probably would have thought you were smoking something provided by one of the park’s then-plentiful dealers.

For its 40th anniversary, Killian sat down with Billboard to look back upon SummerStage’s beginnings, its near-misses and his idea for a free music series that connected all of New York City. Perhaps unsurprisingly, the SummerStage visionary set the tone for the topics before we began.

Joe Killian: Before we start, I have to comment on your shirt – Big Star.

Billboard: Yes, I love Big Star. They recorded at Ardent Studios in Memphis, a great music town.

I booked a show for B.B. King’s 70th birthday [in 1995]. We had everybody from Willie Nelson to Slash, and it was very special. I had gone to the studio that Willie Mitchell recorded all the famous Al Green records. The studio is essentially a little more than a garage. It was pretty funky and ramshackle, shall we say. It’s where Al Green made all those great [albums like] I’m Still In Love With You.

Great album. The last time I was in Memphis I caught the Reverend Al Green’s Sunday church service.

We booked Al.

For SummerStage, during the early years, right?

Yes, that would have been 1991, I think. It was the first booking I had with Al Green, but his stories preceded him. I knew it was going to be a challenge, because it was an afternoon show — Saturday afternoon, three o’clock. So the night before, he was playing the Academy of Music in Philadelphia. I called a friend and said, “Let’s go down. We’ll take the train, we’ll see the show, we’ll hang with the band, and then we’ll stay in the hotel. The next morning, we’ll make sure everything is sorted.”

We do that. Great show, Academy of Music — beautiful, in Philly. Go to the hotel afterward. Everybody’s having a drink or two. “OK, see you in the morning. Bus is leaving at 3:00 a.m.” It’s 10:00 a.m., everybody’s on the tour bus. Al’s not there. Off we go. The tour manager is like, “Al had a friend last night. They’re in Jersey somewhere. He’ll meet us.” There are no cellphones, right?

Well, it’s 1991, of course.

So we pull off at a rest stop halfway. I call everybody back [in New York] from a pay phone and say, “If you hear anything, let me know.” All-points bulletin and all that kind of stuff. They start making calls from here. The bus comes back, the show’s supposed to be at three o’clock. It’s 1:30. There’s no Al. The band is at sound check, but there’s no Al. I’m trying to find anybody.

Finally, I get a call from — I believe — the Holiday Inn at JFK. The manager there says, “We’ve got a guest here. He’s supposed to get to Central Park.” I said, “Yeah — Al Green?” He said, “I don’t know who it is, but he says he’s supposed to get there, and he wants a limo sent to pick him up.” I said, “OK, no problem. Limo will be there. Give us 10, 15 minutes to find a limo company out by JFK.”

We do that. Waiting, waiting, waiting. I tell the manager, “Once he’s in the car, call me, so I can figure out the time. JFK to here, even on a Saturday, is going to take a while.” Maybe 20, 25 minutes later — now it’s after two — he says, “Hey, your guy came out, and it was a black stretch limousine.” I said, “Great.” He said, “No, he wants a white one.” I said, “Did you get him in the car?” “No, he wouldn’t get in. He wouldn’t get in a black car.”

At this point you’ve got, what, an hour to go?

We’re less than that. We got a white limo in. He got there 3:15, 3:20. He came on, and boom, he did his 60 minutes, and he was off. But they were the greatest 60 minutes. His voice was still in great form at that point.

To go back a few more years, SummerStage started out in a different New York City. What was it like when you were putting on shows in Central Park at Naumburg Bandshell in 1986?

It was dangerous. It was not bucolic. You’d be here in the park in the day and get mugged. It was not uncommon, because of delayed maintenance, deferred maintenance, whatever you want to call it. Broken glass everywhere, garbage that was picked up only occasionally.

How did you start booking acts for those early years?

What I did know about the downtown scene, besides my own personal enjoyment, was that those audiences — they may not be big, but they’re loyal. Whether it’s La MaMa or the Joyce Theater, some of the other downtown venues, Tramps, they were loyal fans that would travel to see their artists – if you gave them the right artist. So that was one audience I identified. Then the others; I knew you go to Brooklyn at the time, in Flatbush, there was a massive Haitian community. Tabou Combo was regularly playing every Friday night, Saturday night, doing two, three thousand people. And into the Bronx, a lot of Latin clubs. So you’ve got a mix of downtown avant-garde stuff and then what I would call the great neighborhoods of New York.

What was apparent to me, too, was that there are a tremendous amount of Nigerians in New York. One of the greatest drumming records ever, Drums of Passion, Babatunde Olatunji, he’s living on the Upper West Side [at the time]. There’s a huge Senegalese, West African community: Youssou N’Dour, as an example, would come through, but he would play in a tiny club. Now this guy’s a superstar playing the tiny club. I say tiny — it’s several hundred people, but still. The caliber.

So you identified distinct talents with underserved audiences — no small feat pre-Internet — in a massive city and began booking them. How did you actually get them on stage in Central Park?

When I met with Betsy Barlow Rogers [who helped found Central Park Conservatory], she said, “Hey, you’ve got to meet with the Parks Commissioner, Henry J. Stern.” I said, “Great.” A couple of weeks go by, I meet with him. Henry took to the idea; I don’t think he listened to anything I had to say, other than he talked about opera. Basically, both of them said, “OK, let’s try this out. We have no money, though.” So we scraped together a little bit of money. We built this small series. I got Henry and Betsy on the same page.

I say the same page, they worked very closely together — but they had very different agendas. Betsy’s was to restore the park to what Frederick Law Olmsted [Central Park’s architect] designed. Henry’s was: keep the voters happy. He had been a council member. He was like, “As long as my name is in the press and I can potentially run for office again, let’s go.” He was supportive in that way.

Eventually you moved from the Bandshell to Rumsey Playfield.

So this is our fifth year. We had no money. It was two tin cans and a string. We had a lot of press. The Village Voice, WNYC — very supportive. We had a lot of Flaco Jiménez, Astor Piazzolla — my favorite shows ever. We had a lot of attention, a lot of notoriety, but financially it was very difficult, not reliable, and the Parks Commissioner is right there saying, “Are we going to be able to pull this off?”

Not to jump ahead, but did you think it would last this long?

I’ll say this. It would have been ’89 and Joe Papp, who had started the Public Theater and Shakespeare in the Park, they were celebrating an anniversary, 25 years. They had this reception, and I go over and talk to him and say, “Congratulations — 25 years.” And he said, “Well, you’re doing good work.” I said, “Yeah, good chance we’re not going to be here next year.” It was that tight. Good chance we may not even be able to pay for the season we’re in. We could get to August and say, “We’re out of money.” He said, “You’ll figure it out.”

He talked about his own early days with Shakespeare and how he got what had been the Astor Library — the city gave him the building; it had been abandoned — and he built the Public Theater. I remember saying to Joe, “You’ve got a big advantage. You have Shakespeare. Shakespeare raises money. I’ve got Tabou Combo. I’ve got John Zorn.” Joe was very encouraging. He said, “You don’t know it, but you’re doing something good here. Keep at it, and we’ll see.” He was very optimistic, very supportive, and I’m grateful that he said that. Because when you’re out of money, and you’ve got two seasonal people working for you, and every year you’ve got to hire new people, it makes you want to give up.

Just two seasonal people?

The Parks Department was very supportive, but they were stretched thin. I couldn’t get the site at the Bandshell clean. There was garbage everywhere. I’d be out there cleaning it up myself. I look back now — I would never have believed it survived 30, 40 years. I’m grateful to all the people who kept it alive, and I’m grateful to be on the board and still relevant in some way. We just don’t know sometimes in life.

Was there a point where you thought you had turned a corner in terms of ensuring its survival?

We had Ladysmith Black Mambazo [after Paul Simon’s Graceland], that would have been maybe the second or third year. We were catching on. Again, we didn’t have any money, but there’s a guy, Johnny Rosenwald, who was at Bear Stearns. I’d been introduced to him, and he said, “Yeah, I’ll take a meeting.”So I go to his office over on Park Avenue and 54th, get escorted in. I tell him everything about SummerStage. Somebody had given him a little cheat sheet, so he said, “I know all about it.” I’m in the office less than 10 minutes, and he says, “Call my secretary in a week. I’m going to try and set up a meeting with somebody.” He didn’t even hear my pitch, but alright, I’ll do anything.

A week goes by. I talk to the secretary. She says, “Yeah, next Thursday.” Meet Johnny in the office again, up to Park Avenue, up the elevator. He says, “OK, we’re going to go meet somebody. You’re going to have 60 seconds. I don’t want you to go longer than 60 seconds. Whatever you do, give them your story in 60 seconds, and that’s it.” OK. Johnny’s a good guy, but a real Bear Stearns banker. And I can tell this man has something here—he’s not taking time out to be nice to me. We start walking up Park Avenue, about two or three blocks, and we are standing in front of the Seagram Building. I know architecture a little bit, so I know it’s a beautiful building. Beautiful day. He says, “Come on, let’s go.”

We go in the elevator, we’re in the Seagram Building, and sure enough, a few minutes later, we’re escorted into Edgar Bronfman Jr.’s office. At that time, he was running the Seagram family — the Seagram spirits—before he would acquire Warner Music, before all of that. We go in, and they’re talking. The light goes on for me: this is how New York is made. So I started talking, and I see Edgar Bronfman Jr. behind his desk waving at me like, “Stop,” and I’m thinking, “I’m dead. I’m a dead man.” But he said, “A couple weeks ago, we acquired Tropicana Orange Juice. What if we did a marketing deal with you? Let’s call it $200,000 a year for three years.”

That’s a lot, especially back then. When the city was broke.

It was a good vote of confidence.

In those early years, you booked the acts, yes? And it was only Central Park then, no shows in other boroughs?

I booked every act…. we could be creative in what we put in here. The word “curate” is overused, so I won’t use that—but we could be very creative. To me, Central Park was the great place of democracy—seriously—that nobody owned it. If you go to a certain park in the Bronx or Brooklyn, that neighborhood, somebody, quote-unquote, owns it. At that time, a lot of drug dealers owned the parks. Literally — they were their parks. But nobody could say that about Central Park. It was too big. The democracy of “anybody could come here” — it wasn’t that the park was white, wasn’t that the park was Black, wasn’t Latino. There were certainly gay sections of the park. It was a park for all people, and I knew that’s what the series could be.

No one owned it, you could loan it for a night.

Now it gets to be year two or three. I could see that both Betsy and Henry were surprised by some of the programming. I think they expected more cover bands, more middle-of-the-road stuff. I knew that’s not going to give [SummerStage] a long life or an identity. There’s nothing creative about it as a producer. It’s like weddings or something. It’s not representative.

Sure, not representative of New York City. SummerStage has sounds from around the world, many of them performed by artists who live in New York City. The first year was Sun Ra, not a local. What motivated you to seek him out for the inaugural year?

I had seen Sun Ra a number of times — he always played Detroit [where Killian was raised]. When I saw him, he was based out of Chicago. There was that whole Art Ensemble of Chicago that would always come through Detroit. I always loved Sonny because it was spectacle. I don’t think the word “Afrofuturism” existed then, but he was not of this world. He was a bandleader, a great arranger in the traditional jazz sense, but in a very avant-garde sound, with a theater around it. He was a Black man, but he was living in outer space.

So I booked him at the Bandshell. Two of his band members came up the day before to get paid in cash. Everybody arrives, Sonny arrives. He had a big Cadillac. He’s in the back seat, and I go over there to introduce myself, and there’s a woman shaving him. Sonny’s talking. It was a little overcast—I thought it was going to rain. He says, “When Sonny comes, the rain goes away.” He did it in his very rhythmic way, and to me that was the essence of cool.

And Fourth of July, a couple years later, with Sonic Youth, it was one of the most famous [SummerStage] shows ever. Kim Gordon still refers to it. You could see the connection between Sun Ra and Sonic Youth, the way they each built their views and orchestrated. Flash forward: two years ago, Kim Gordon plays this stage again. That’s a beautiful long run.

As an attendee, I can say it’s easy to keep coming back because it’s just a lovely space to be in.

I’ll tell you, there were some days here in July and August where it’s in the 90s, you’ve got 5,000 to 6,000 people sweating and drinking beer, and you smell both beer and sweat. There’s nothing like that. That’s the thing I kind of realized: Central Park is a big tourist place. You could allow people to come in—maybe they stay for 15 minutes, maybe they like it, they leave, maybe they get turned on to some new music. The artist was number one, and the audience was number 1.5 — because the audience had big ears. They were curious New Yorkers. I’ll say “intellectual,” but that doesn’t mean book smart. It means they’re listening to a bunch of stuff. They’re interesting people.

“Big-eared” is a great way of putting it.

They would come back. They built a trust in SummerStage. “I don’t know who this is, but if it’s at SummerStage, we’ve got to go check it out.” That, to me, was heartwarming. You’ve got that kind of strength — even if you don’t have the money, you have that kind of community.

That’s what keeps something alive year after year. So you eventually stepped back. What motivated that?

I left in the spring of 1993, and I had booked every show up until that point. I was just tired. I was here 40, 50 shows a season — I wasn’t tired physically, but to your earlier question of “when did you turn the corner”: I knew at that point we had turned the corner, and that this was going to have legs. It was like a child that I had raised, and you’re going to go off to college—or in this case, your parent is going to let you go — because I knew it required a whole different set of skills. I had kind of made that decision, and then fortuitously — I love how it happens — I got a call from Radio City. They wanted to add shows and book shows around the city. I thought, “OK, this is another platform. Let’s go and try it.” I’d already revamped Central Park, so let’s go.

Before we leave Central Park, I wanted to ask this: in the early years, you didn’t have proper ticketing. Was it just people wandering in? Was there any sense of crowd control?

Starting in the first season, ’86, NYPD would not allow night shows. They told us the park was too dangerous; they couldn’t guarantee security. So we only had three o’clock afternoon shows for a few years. Then they started allowing us to do a few night shows at the Bandshell. Once we got [to Rumsey Playfield], we could do whatever — we could control it a bit more. I say that because night and day, there are different audiences and different reactions — or fans.

You’ll find more families during the day, kids.

Exactly. We had NYPD security, but we also had private concert security. There were shows where we did have to close the gates effectively and ask people to sit outside. But yeah, people wandered in. That’s how it was. I remember when we first moved [to Rumsey Playfield], I thought, “OK, now there’s a chance that we can sell beer, because we have a perimeter wall, and the police would allow it.” But they would not allow it. Henry said no.

So I finally brought the deputy commissioner over to this site. Right here, there were four or five guys in grocery store carts with plastic bags filled with ice and beer. They were selling beer everywhere. So I said to the deputy commissioner, “Beer is sold here. Why don’t we sell it? We can control it, we can check ages, make sure people are legal, and we’ll make a few bucks for the series.” He thought that made a lot of sense, because he was appalled that NYPD was doing nothing. These guys were selling out of grocery carts.

That’s kind of a risk, to bring him there and then be like, “Hey, look.” He could have gotten angry and been like, “What the hell are you allowing this for?”

Oh, I think he was, but he knew that there was nothing — NYPD wasn’t going to do anything. “Solve my problem. What do you want to do?” The one thing about those cart guys, like the skaters and all — the word is not “resilience,” what is it? They were entrepreneurs.

Tenacity, maybe.

That’s a good one. They were tenacious. They were great New York cockroaches.

Like a cockroach, you couldn’t kill them.

You could scatter them away, but you couldn’t kill them.