If you ever stepped foot in Jack Ryan’s back in the day, let’s just say… hunnni got a glow-up. Enter: Jack’s Extra Fancy. Think—if That ‘70s Show and Saturday Night Fever had a baby, and that baby boy grew up as the kid who threw legendary disco parties.
On this particular night, I popped in for a whiskey and yap sesh with a friend. One drink turned into two, and before we knew it, Jack’s became the first stop on our way to nightcaps at Lucky’s. But let’s not skip ahead—let’s talk about the main character of the story.
The scene: Baywatch reruns playing next to the basketball game, a rogue rabbit head mounted on the wall like an inside joke I’ll never be in on, a funky bear vibin’ in the corner, Johnny boy lit up under neon lights, and a disco ball that’s completing the lewk. It’s weird. It’s wonderful. It’s working.
The menu: Short, sweet, and covers your booze-eats. You’ll find hoagies and grinders, smash burgers, chicken poppers, sticky buns slathered in icy goodness—the kind of stuff that hits just right after drink number two. Order the chicken hoagie, it’s pure duch*.
*Duch aka Duchess: my term here used to describe something delish. Not quite the Queen B, but just Duchess enough—she leaves you satisfied and feelin’ fancy.
Flashback to my first visit at my good friend Jack’s—I ordered a martini that came garnished with a pepperoncini. For me, this is everything. I’ve been sipping what I call a Marchini for years. The recipe? Gin, one ice cube, pepperoncini juice, and a toothpick skewer of your fixings (cue in the chedda and pepperoncinis, plural). It slaps. Recipe handed down by the man, the myth, the legend: The Paps, Mr. Biggie Smalls, Captain Red Beard, Big Daddy Big Big, my dad. We like it spicy. So although it may not be an exact replica, a round of applause for the guy or gal responsible for slapping it on the menu.
But tonight? I kept it classic. Whiskey, neat.
And let me tell you—the whiskey was flowin’ so one turned into two, and before you know it, I’m taking snaps in the bathroom mirror like every other girlie on the block.
Jack’s is the kind of place that makes you wanna stay a while and chill. It's an elevated dive with a twist. It’s chill enough that you don’t feel like you’re trying too hard, but not so divey that you leave smelling like regret.
The residence: Winton area—known as the up-and-coming neighborhood with good eats like Wildflour and Lucky’s, the Winfield—the bar you somehow always keep coming back to—and JJ’s for when you’re 4 or 5 drinks deep and think you can belt out tunes for karaoke like it’s nobody’s business—Miss You by Blink182<3
The crowd: Grown but not boring. Unpretentious yet bold. The kind of people who’ve outgrown sticky floors and Red Bull Vodkas but still know how to have a good time. They’ve got stories, they’ve got style.
The energy: Just enough disco, just enough low-key. The music gives ya a wink to the past while keeping the vibe smooth and current. It’s the kind of place that lets you be you, whether you're dressed to impress or just stopped in on a whim. A spot where a 30-something won’t feel like the elder at the bar or embarrassed for not having a TikTok. Honestly, it draws all walks of life, and no one feels out of place.
When you visit Jack, take him for who he is. Extra? Maybe. Fancy? Semi. Just enough quirk, just enough nostalgia, and just enough whiskey that may leave you under the disco ball saying, “Heeere’s Johnny.”
