What better way to celebrate turning 50 than throwing a party.
But after 30 years in entertainment, Bootsie felt it called for more.
“We contacted some of the top artists in the industry and we’re gonna do the big 5-0 on stage,” said the comedian.
Robert Atwood will lead the 16-piece Wall Street Band at what promises to be a lively night this Sunday at Ruth Seaton James Centre for the Performing Arts.
Jessie Seymour, Olivia Hamilton, Lloyd Holder, Laurita Adderley, Sheila Smith, The Euphonics, and the Blues Band have all signed up to perform.
“These are the top artists in Bermuda,” said Bootsie, who was born Earlwin Wolffe on February 15, 1967.
“It’ll be laced with comics throughout the show — all local — Jah, Nadanjah, Gina Love and Robert Somner. The birthday boy also promises to perform.
“We’ll see how the night goes, but whatever it is, trust me, I will entertain you,” he said.
Bootsie got into comedy in the 1980s, inspired after seeing Whoopie Goldberg perform.
“She’s amazing. She did a one-man, Broadway show of different characters depicting social issues.
“I saw it on videotape. They had video tapes back then,” he laughed.
“When I was young, all I did was joke around. I always practised skits and characters.
“As time went on, I developed a bit of a Bill Cosby style; the influences that kind of shape you. George Collins was another one. He’s unbelievable. Then of course there’s Eddie Murphy, but Whoopie was definitely one that I modelled my whole act behind.”
He held his first solo show at Ruth Seaton James in 1990. He still doesn’t know if it was “arrogance or confidence” that led him to book it for three nights.
“That place held 680 people at the time and I sold out every show,” he said.
“I started to get booked so much that I decided to turn some of my skits into stand-up material.
“My career took off to another level. I joined a group, Creative Perceptions with Patrice Frith Hayward. We went overseas to Carolina in the National Black Theatre Festival.
“When I came back that’s when I really branched out to my own thing.”
Russell Simmons saw him performing his own skits on a gospel tour through upstate New York and he got picked up by Def Jam. He taped a season with them, but his material was too family-oriented for the group.
“I grew up in a church, but I think one of the reasons why I’ve lasted so long is the fact that I chose not to use profanity on stage and that landed me doing all sorts of events — birthday parties, weddings, retirement parties, Christmas parties, church functions.
“Not using profanity worked in my favour. It kept me working because people felt confident that there wouldn’t be a slip into colourful words.”
He’s opened for big name acts such as Luther Vandross and Bill Cosby and now lends his voice to radio, leading the morning show from 9 to 11 on Magic 102.7.
“I first ventured into radio in 2005,” he recalled. “Inter-Island Communications said why don’t you try out for the 90-second comedy spot?
“[They said], ‘You didn’t get the job as the comedian but we were wondering if you interested in being the anchor?
“I never even listened to radio. The only time I ever did when I was checking to see they were playing my commercial.”
His show on Hott 107.5 ran for a year and a half.
“I went in one day and at 5.30 in the morning they fired me,” he laughed.
But that blow brought new opportunities. He ran his own club, Bootsie’s, on Front Street, for a steady seven years.
“At that time I did a lot of promoting. I brought in a host of comics, namely Dave Chappelle, Joe Tori, Mike Epps — he was actually a friend of mine. I knew Mike Epps before he was Mike Epps.
“I promoted Boyz II Men with Glenn Blakeney for a Valentine’s Day show — that was probably the biggest.
“We had a couple of selling years but then the economy went bad.”
Lesser known is his work within the community, specifically with the Department of Education.
“I worked with at-risk behavioural children from 2001 to 2005.
“These were young people that were labelled as not being able to function in the regular school system. I say ‘labelled’ and I use that heavily,” he said.
“There was a team that dealt with these beautiful young people. They had to be groomed and nurtured.
“That was one of my greatest passions. I loved that more than being on stage.
“We were trained at Cornell University [in a] system called therapeutic crisis intervention.
“It’s an amazing system. I was learning things about myself. It helped me in my personal life.
“That is a part of my life that I really cherish.”
He returned to radio with the release of his much loved song, Bermudians Love to Drink, and delved into ventriloquism at Grotto Bay Resort with his puppet Reggie.
“Reggie is a fast-talking, quick-lipped figure. I got to pull him back because of what he wants to say. I have to keep him from using profanity.
“I sometimes take him to bars, I just show up. He’s like my pet. We sing karaoke,” Bootsie said.
His biggest accomplishments, he said, are his “three wonderful children”: Ashun, Akeem and Aalai Wolffe.
• Tickets, $50, available at 27th Century Boutique, bdatix.bm and at the door. The show starts at 7pm doors open at 6.15pm.