Funny business: Bob Shoemaker and Coconuts Comedy Club

It’s been 32 years since Bob Shoemaker burned his last necktie, stuck his law degree in a bottom drawer and bet the farm on a St. Pete Beach nightclub.

At 70, he’s yet to look back. Coconuts is now the oldest continually-operating comedy club in Florida.

“I’m not rich,” he says, “but for me it was never really about the money. I just wanted to be able to do what I wanted to do.”

During its peak years, in the late ‘80s and early ‘90s, there were Coconuts in 20 locations around the country. Shoemaker had one in London, too, and another on Grand Cayman Island. He figures he’s employed about 1,200 comedians over the decades.

Today, there’s just the cornerstone club, an intimate room in a Gulf Boulevard strip mall.

In 2016 Billy Gardell of TV’s “Mike and Molly” returned to Coconuts, where he’d been a regular performer, to say hello to Bob Shoemaker and office manager Jackie Manning.

There have been big names, mostly as they were on their way up. Jim Breuer, Billy Gardell, Larry the Cable Guy, Darrell Hammond, Jon Stewart and the late, great Mitch Hedberg were frequent performers at Coconuts.

By focusing on young, hungry comics, and steering clear of the top-dollar headliners, Shoemaker was able to keep his overhead low while developing Coconuts’ reputation as a showcase for new talent.

When he first started booking comedy, part-time, he’d never seen stand-up, except on TV. In the early 1980s he and a couple of friends were promoting concerts in the banquet room of Las Fontanas, a Mexican restaurant by the St. Pete/Clearwater airport.

The city’s only comedy venue – on Tierra Verde – was closing. The club’s financiers approached Shoemaker and his partners with an idea and an offer – can we do comedy at Las Fontanas? “At that time,” Shoemaker laughs, “people had the perception that we knew what we were doing.”

The truth was that he was already bored with practicing law, and as a member and co-manager of the country/rock band Tom Gribbin & the Saltwater Cowboys he’d toured Europe, and seen enough of show business, to know he wanted more of it.

At Las Fontanas, he got a crash course in the business of laughter. “It was hard to get there – you had to drive through a trailer park,” Shoemaker says. “But I noticed that people were coming for this comedy thing.” They created their first “club” in an unused loft space.

“After the shows, the comedians and I would go down to the restaurant. They’d eat something – tacos or whatever – and they’d talk. That’s how I learned everything about the comedy business, sitting in the booth and listening. They’d tell me about all the other clubs around, how it worked and how this was different from that. I just listened, and took it all in.

“With the band on tour, I was always in charge – we’d have 60 road cases, nine guys and a soundman, hotel rooms and all that. And I’m looking at the comedy stage – there’s one mic and one stand. And I’m going ‘This is easy.’”

Soon enough, the restaurant owners pulled the plug. But Bob Shoemaker was determined.

“I stayed up all night with my pen and paper. I was running figures and just thinking about it. And the next day I went to Tom and said ‘I’m staying in this business.’”

Bob Shoemaker devised a radical – and risky – business plan. “Originally, this is how it worked if I paid out $3,000 for a show: The headliner got $1,500, then $1,000 for the middle and $500 for the other guy.

“But I noticed that out here in St. Petersburg, Florida, the big names who were used to playing the big rooms in Vegas or New York, they were kind of phoning it in. Whereas those middle guys – who wanted to be the headliners – were terrific. They dialed it up, and they were real funny.

“So my whole thing to stay in the business was this: ‘I’m going to stay in, but I’m cutting out the headliner.’ I decided to cut the budget in half – and I’ll do enough business and not lose money. Pretty simple, really.”

From Las Fontanas, Shoemaker went to the Howard Johnson’s on St. Pete Beach, negotiated a deal with the lounge owner, and the first Coconuts was born.

“I told him: We’ll keep the door, and $1 from every drink sold during our shows. I said ‘You keep 100 percent of what you sell, and I’ll get 20 percent of the gross.’ With no liquor license or nothin.’ That was a really good move on my part.”

There’s never been a brick-and-mortar Coconuts Comedy Club.  “I never had any money,” Shoemaker says, “but I didn’t have to buy a venue, I didn’t have to rent a venue, I didn’t have to have a liquor license. In every town, we had our logo there, and we had deals with the venues, but it was almost like a band coming into town – you play the gig and you move on.”

The real value was in the brand. Still is. Shoemaker and his office manager Jackie Manning rarely deal with booking agents or managers; the comedians set things up themselves. “They like Jackie, and they like me,” he explains. “And they like where we are! We live in a beautiful place.”

Karl “Special K” Douglas performs for a sold-out Coconuts crowd in early March.

They also like the intimate space, where they can see an interact with the audience.  The big comedy clubs across Tampa Bay can – and do – handle hundreds of customers. Coconuts’ capacity is 80-84 people.

Coconuts and Howard Johnson’s parted ways after 18 years. Afterwards, the club was anchored in several different beach hotels before landing in its current spot, attached to MJ’s Sports Bar, in 2014.

Shoemaker says this is the best room he’s ever had. “It’s a replica of the original Improv in Hell’s Kitchen in New York City,” he explains. “One of the places where all this started 50 years ago. I tell these young comics that need to appreciate that this is the atmosphere and the type of place that inspired Richard Pryor and George Carlin … the whole business, really. They were real funny, but they were in an environment that was just perfect for them to do what they did.”

All Bob Shoemaker ever wanted to do was make people happy, and hopefully make a living at the same time. The comedy club business isn’t what it used to be – he’s pretty sure he’s never going to get rich – but Shoemaker may yet have the last laugh.

“When we first started at the Howard Johnson, it was five bucks to get in, and we had 300, 400 people a week,” he chuckles. “Now it’s $20 to get in, and we have maybe a hundred people. It’s the same money.”

Visit Coconuts Comedy Club here.