The Gulfport Neighborhood Guide: O’Maddy’s, oh, man

A few nights of adventure at Gulfport’s storied karaoke destination

click to enlarge O'Maddy's Bar & Grille, located across the street from the Bert and Walter Williams Pier on Shore Boulevard - Chip Weiner
Chip Weiner
O'Maddy's Bar & Grille, located across the street from the Bert and Walter Williams Pier on Shore Boulevard


I have a new friend in Baby Jesus and he’s about to perform an Eminem track, “Without Me.”

He insists he’s either going to jump-start the party or trigger the crickets on this Wednesday night edition of O’Maddys’ karaoke night, which is scattered with middle-aged regulars, some 20-somethings getting Hump Day soused, and a gnarly beardy dude who selects shuffling blues-rock numbers and plays harmonica instead of singing (harmoni-oke?). Right now, a couple’s on stage wailing through Mötley Crüe’s “Home Sweet Home” as if it were a duet and clutching each other in a slow-swaying embrace during the instrumental breaks.

Baby Jesus, aka David, is the first person I meet at the Gulfport waterside bar and grill renowned for its nightly karaoke shennanys. O’Maddys is ripe with people-gawking opportunities, and those single-serving friends you make when you’re both enjoying (or enduring) the same experience. There’s an overall beach-vacation vibe amidst the blue-painted walls and bright patio furniture, though the karaoke crowd throws it all into a tailspin of human miscellany.

Baby Jesus tells me his nickname as we bond over hip-hop and drunken stupidity, and nurse drinks perched along a stretch of mosaic-tiled bar. He likely earned the nickname for his general Carpenter looks (though his dark eyes aren’t warm and forbearing but hard and glittering with mischief) and petite stature (the perfect height for motor-boating). But I wouldn’t be surprised if it was prompted by his delicate long-fingered hands or the way he carries himself with such incredible self-confidence, which only improves his stage presence as he spits the quick-fire verses in Eminem’s track with impressive ease, even getting us all to chime in during the “Guess who’s back?” chorus. I think, ‘Hey, if he can do this with so much conviction, then fuck, I can, too.’

But I’m only here to soak up the vibe. The real high dive is Friday. Baby Jesus and I conspire to meet up again and slay some hip-hop tunes then, before a full-bar Zac Brown Band singalong prompts my hasty exit. Plus Baby Jesus is catching vibes from a feisty free spirit and I don’t want to interfere with his game.

***

Baby Jesus stands me up. Not that we really had a date or that I expect him to be hanging around. But, still, I had fantasies of us sneering through a “Regulate” duet and am disappointed I won’t get to live it out for real.

The First Friday street festivities have just ended, and O’Maddys isn’t too crowded when I arrive, though it’s drawing a steady flow of foot traffic in and out, many from Salty’s next door. The ones who stick around are a diverse if slightly younger-leaning lot, and the song selection reflects it: ’90s grunge, Janis Joplin, Sonny and Cher, Prince, some pop-country I can’t begin to name. One of the night’s highlights comes by way of Rocky, who replaces Baby Jesus in my heart.

The 71-year-old gent wears a black silk shirt with white polka dots, and I feel an instant bond since I’m sporting a bra in the same pattern; plus, his sweet-faced smile reminds me of Jack Lemmon. Rocky has already warmed his pipes at another karaoke joint in town, but stopped into O’Maddy’s because he isn’t quite ready to call it a night. He admits he’s concerned about how well his song – an old romantic pop ode, “I Can’t Get You Out of My Heart” – will go over, and he sips a glass of merlot to calm his nerves. When he jumps up to deliver his serenade, I scream for him like a cheerleader on crack, piercing and impossible to ignore, but he has nothing to worry about with his smooth, Sinatra-hued vibrato; the crowd eats it up. He encores a little later with a peppier number, “Mack the Knife,” and I shred my throat cheering for him again.

I’ve dragged along my younger cousin Andrew (on both trips), and he’s hating life right now, wanting to leave as soon as he finishes his second Guinness, but I promise him a few more for his pseudo-patience; he grumbles, but sticks around ’cause the kid likes his alcohol. So he’s slouched all brow-furrowed at the bar when the night’s second highlight hits the stage: a dready black dude roaring Pantera’s “Walk.” My cousin loves that band, has Pantera tributes tattooed on his arms, and gets all emo on the date of Dimebag Darrell’s death, so I nudge him, hard. “Hear that? And you wanted to leave.” Before I can rag him some more, I get called up for my moment in the karaoke spotlight.

My usual fallback is “Bohemian Rhapsody” — always go with what you know no matter how high your liquid courage is running — but tonight I choose “The Joker” because it’s shorter, everyone knows it, and I can sing it from memory. Only I forget how low Steve Miller’s vocals go, and I can’t quite hit the “’Cause I’m right here at hooome” notes properly. But I kill the “Really love your peaches, wanna shake your tree” parts and even get some audience love at the song’s conclusion.

As we head out, I realize it’s a good thing Baby Jesus didn’t show; I might’ve had a few too many, let my liquid courage turn to overconfidence, and decided I could tackle Iggy Azalea’s “Fancy.” 

O’Maddy’s Bar & Grille hosts karaoke every night beginning at 9:30 p.m., at 5405 Shore Blvd. S., Gulfport, 727-323-8643, omaddys.com.

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