Sing your heart out at these Island karaoke haunts

John Curran performs at the Ritz, and also hosts karaoke at the Island Bar and Grille. — Photo by Tom Stevens

We’re all guilty of singing when no one is looking — the shower, the car — but how about stepping onstage in front of strangers, or even worse, friends, and belting out an old classic? Thankfully, there’s a venue for that. Some of your favorite Island hotspots feature regular karaoke sessions, where the live entertainment is our favorite guilty pleasure: people watching.

The Ritz in Oak Bluffs holds weekly “Stupid Fun Karaoke Nights” on Monday. The show starts at 9:30 pm and goes all night; we’ve heard it gets really good after 11:30. The night is usually capped off with a heartfelt community singalong to a classic by Journey, Elton John, or Billy Joel. MC Tom Stevens has fun, and has created his own alter ego to go along with it.

Luckily for novice singers at the Ritz, Tom has a background in music and recording, so he’s likely to make you sound better than you actually do. “If the people can’t sing, I give them more reverb or delay and bring the levels down; I’m focusing on the overall sound,” said Tom. “But the worst are the people that can’t sing and don’t know it.” Touché, Tom.

Next door at the Island Bar & Grille, also on Circuit Avenue, weekly karaoke kicks off this Thursday, May 21, with new MC John Curran. John has his own karaoke business, Shining Star Karaoke, and he formerly hosted the Island’s own shining stars at the P.A. Club. John brings 20 years of karaoke experience, and will be organizing a weekly, summer-long Vineyard’s Got Talent contest; the top three will be announced at the end of the season. Contestants will be judged on vocal ability, stage presence, and interpretation. It’s time to start practicing.

If you’re looking to sing your heart out in Edgartown, veteran Island entertainer Dan Cassidy hosts a karaoke show at the Wharf every Friday night (summer schedule may vary). Prior to the Wharf, Dan and John Tiernan, a.k.a. “Johnny Showtime,” used to MC at Season’s, so he knows his stuff. The two have hosted karaoke at the Wharf together over the years, and have made some good memories. “There was one time I got up to sing to get the night going, and I found out later that Kirsten Dunst was in the audience … she didn’t stick around,” said Dan. He appreciates his usual cast of local regulars, and likes to have fun with tourists too. “When people are down on vacation, they want to have their chance for a Vineyard memory, so it’s important, whether you’re a regular or here on vacation, you get your chance.”

You can check out some epic photos from the Ritz’s karaoke nights on their Facebook page at To find out more about John Curran’s Shining Star Karaoke, visit or call 575-538-1169.