They are the most successful R& B male vocal group of all time and have sold more than 60 million records. This summer they are playing a casino in Detroit, Cardinal Stadium in Louisville and doing a three-night stint in Las Vegas.

And on Thursday, Boyz II Men will come to Outerland.

on the couch
Whitney Dailey and Mona Rosenthal say it’s tricky to predict which acts will sell. — Jaxon White

The nightclub near the Martha’s Vineyard Airport is already fielding e-mails from fans and selling tickets at their box office. For weeks, talent advance manager Whitney Dailey has been on the phone with the band’s agents. Whether by e-mail, telephone or in person, for acts big or small, nearly all conversations at Outerland begin the same way. “The question we always get is, why do tickets cost so much?” said Mona Rosenthal, a club owner and director of information services.

There is a one-word answer: overhead.

“Ticket prices reflect what it takes to bring an act here,” Mrs. Rosenthal said. “Our overhead costs are astronomical.” Tickets for Boyz II Men are $49.50. The most expensive act this season, Taj Mahal, cost $60 to attend. One of the least expensive performances will be tonight, when John Cruz takes the stage to celebrate radio station WMVY’s 25th anniversary. Tickets are $10.

Grace Potter
Superb shows from Grace Potter no matter crowd size. — Jaxon White

The nightclub got its start in 1979 when it opened as the Hot Tin Roof, a summer music venue. Owners included Carly Simon, Herb Putnam 3rd and West Tisbury resident George Brush. In 2006, Mona and Barry Rosenthal, along with Mr. Rosenthal’s brother Arthur, bought the Roof, as it was affectionately known, for $660,000. Mr. Rosenthal had dreams of staying open year-round, hosting all-ages events and running a fine-dining restaurant inside. The year they opened, the only other local nightclub, the Atlantic Connection on Circuit avenue in Oak Bluffs, closed its doors. Things looked rosy.

But in the three seasons the Rosenthals have owned the club, a slow economy and an out-of-town location have combined to make the business a difficult place to operate at a profit. Mrs. Rosenthal would not comment on whether the club makes money, but operations director Dave Dunbar did say it is making more than it did last year. “Sales are up over last year, both in alcohol and on overall sales,” he said.

Although Mrs. Rosenthal and Ms. Dailey are constantly asked about the price of tickets, they say in fact the cost to see a show there has not changed over the years. “We actually have not raised ticket prices at all [since it was the Roof],” Mrs. Rosenthal said. “And band costs have gone up. Overhead has gone up. Expenses have gone up incredibly.” So why not raise prices? “There is only so much the Island can bear when we have so many events one after another,” she said.

Ms. Dailey said it costs a few thousand dollars just to open the doors of Outerland — or to keep them closed. There are electricity and water bills, a mortgage, staff to pay and insurance for each act which takes the stage. And that is just the beginning of the list. “Whenever I make that first contact with an agent, I immediately tell them, we are a 700-capacity family-owned nightclub, which is rare in this industry, and we have overhead like you’ve never seen before,” Ms. Dailey said.

She and Mrs. Rosenthal are the undying energy behind Outerland. Mrs. Rosenthal handles publicity. She updates the club Web site regularly, sets up ticket sales, orders posters and organizes advertising. She also washes dressing room towels after each act leaves and bakes homemade brownies before each new act arrives. “Citizen Cope actually put Mona’s brownies in his rider,” Mrs. Rosenthal said proudly.

Both she and Ms. Dailey are at the club every day it is open. And they are there at night, greeting the entertainment for sound check and ushering out the concert-goers at the end of the show. “I get in bed at two a.m. and then wake up in the morning, take a shower and go right back to it,” Ms. Dailey said.

In December and January, Ms. Dailey, 23, begins researching the acts — the club books bands, deejays, comedians and hosts events like an annual hunky carpenter contest and film screenings — which she hopes will draw crowds. In February, she begins placing offers, a difficult thing to do since most bands do not have the Vineyard on their tour schedules. “They call it a one-off,” Mrs. Rosenthal said. “If they’re playing anywhere in New England — Boston, New York — one-off is Martha’s Vineyard. It is one off their route.” Added Ms. Dailey: “Agents tell me they don’t come to Martha’s Vineyard to make money. They come because it’s in between two places where they’ll make money.”

Negotiations are often complicated by riders and a wish lists from the bands. “The band may make requests that might not be available on Martha’s Vineyard because we’re on an Island, or, if they are here, it costs three times the amount,” said Ms. Dailey. So frequently, she has to refuse things. This summer refused items included six dozen de-thorned roses, three dozen brand new bath towels, one bottle of Cristal Champagne, a carton of cigarettes, one bag of 12 unopened men’s white tube socks for a single performer and 26 Rough Rider condoms for a two-person band in town for one night.

And then there are the ferry reservations. “Eighty per cent of ferry reservations inevitably get changed to a different day, a different time or a different vehicle,” she said. “I have a five-page grid that I update every single day just for the ferries. The wait list alone is two pages long.” Outerland pays to bring their acts to the Island. Most acts bring a tour bus. Some add to that a trailer. Ferry ticket prices range from $370 to $450 depending on the length of the vehicle. Often the club also provides on-Island car rentals and taxis. Sometimes they must arrange water taxis for acts booked at the last minute when the ferries are full and reserve a car service to pick up performers at Logan Airport.

Ms. Dailey also reserves hotel rooms, another cost the club incurs. “The challenge with hotel reservations is that there are few hotels on the Vineyard in the summer that rent rooms for one night. Most have a two-night policy. So we find places that are more accommodating to the needs of local businesses,” she said. “We’re all in this together, trying to bring entertainment to the Island.” Hotel needs can range from one room for a deejay to the 13 rooms the reggae act Morgan Heritage booked. “Some of the reggae acts are huge,” Mrs. Rosenthal said. “The bands themselves are eight people deep, then they bring their merchandise people, their security people, their production people.”

Martin Sexton
Martin Sexton returned to sold out crowd. — David Welch

But these performers also bring in the most money. “We don’t make money on ticket sales,” Mrs. Rosenthal said. “We make money on liquor sales.” Reggae shows attract younger crowds and younger crowds spend at the bar. But the club cannot book a reggae act every night of the week.

“The demographics of the Island are changing and it makes it more difficult to program,” Mrs. Rosenthal said. “There are more middle-aged people on vacation with their families and we obviously want to program with them in mind, but they don’t necessarily make money for us.”

A recent example was Jefferson Starship, the classic rock band that played the club on July 25. “This is an iconic, legendary group that plays stadiums and festivals,” Mrs. Rosenthal said. The night after playing Outerland, the band took their tour to Europe. The night before coming here, they played Newport. Tickets for the show were $40 and only 200 people showed up. The club ended up losing money for the night. “This year with the economy, the shows we thought would sell out didn’t,” Mrs. Rosenthal said.

So the club has scaled back operations. Last summer, it was open nearly seven nights a week and operated a restaurant inside. This summer, the doors are open Wednesday through Sunday with an occasional show early in the week. Kitchen space has been leased to Smokin’ Bones, the Oak Bluffs barbecue place. Some creative programming, including a weekly deejay dance party and a Saturday afternoon backyard barbecue with live music, was canceled due to poor attendance. “At the end of the day, we’re a destination live music venue,” Mrs. Rosenthal said. “People are going to come to Outerland if there’s an act they want to see. So we are having fewer events, but booking bigger acts with names people will recognize.”

Certain acts are guaranteed crowd-pleasers. “The Boogies,” said Ms. Dailey. The club has booked the disco cover band multiple times throughout the season and tickets are $15. This past Monday, the Wailers performed to a packed house. Repetition also sells. Citizen Cope sold out this June, as did Martin Sexton, who played last week. Both shows had ticket prices of $35 and both acts played the club last year.

Reggae acts such as the wailers brings in crowds that spend at the bar, where the money is made. — Jaxon White

Whatever the act, the size of the audience remains hard to predict. “Primarily because we’re a resort Island, people wait until that week to buy tickets,” Mrs. Rosenthal said.

The two women work in a male-dominated industry. “The agents are male, the tour managers are male, most of the bands are male,” said Mrs. Rosenthal. But both love the work. “You have to have a passion for the music,” Mrs. Rosenthal said. Ms. Dailey agreed. “It’s hard to go home once the band goes on stage,” she said.