Of all the gin joints in all the towns in all the world, I walk into Henry and Oscar’s. Although the 4th Ave. and Vine bar is more of an immersive lounge than it is a typical gin joint. Think fur-coated booths, engraved personalized glassware for regulars, and four walls of plasma screens for those lucky enough to be in the back room. It’s exactly what you’re thinking — dinner and a movie. Henry and Oscar’s is owned by the people behind Big Picture, and after drinking the Bogart, it’s one of my new favorite haunts.
It’s always nice having a friend on the inside give you the scoop, and I’ve always wanted to be that friend. So here are five things to know before ordering at Henry and Oscar’s:
1. The bar feels made for the customer. In the front of the house, there are literally fireside couches. Forget the bar stool — why can’t I drink cocktails on couches more often? Mohair lines the high-backs for total cush, you’ll find privacy and expensive attention to detail at nearly any angle, and the cocktails are classic adaptations, stiff, and rarely exceed $10. It feels like, for once, the bar had the drinker in mind.
2. It’s $18 for a personalized, engraved glass of choice. Drink included. You know how only the classiest of places have the throw-back to old world dining with personal liquor cabinets? Well, I like the different angle Henry and Oscar’s took. Instead of a locker to store your booze, you can buy a personalized, engraved glass of your choice, kept in-house, and ready for your favorite drink whenever you dine. Best part? It’s only $18 to do so (I double-checked) and your first drink is included in that price. Glassware options are rocks, wine, or martini — per what you fancy most — and the cabinet is already getting full.
3. Forget the calories. Order the meat. In addition to the typical before and after happy hour times, they also feature a special, fresh-that-day option that unquestionably goes for $3.50. When I went, it was house-rolled lamb meatball sliders, with a fragrant mint jelly glaze and slaw. The offerings are always changing for the extremely happy hour feature, but ohmygod don’t miss the Chicago dog (6.25 during HH) of Vienna beef smoked in Mac & Jack’s beer, with all the Chicago spicy fixings. HH is all day on Sundays and game days.
4. Film screenings in back, bar in the front. The owner is a third generation theater owner, so you know his crew understands an audience and a movie. When there, ask to be seated in back room, where the lights are dim, the screens can be selected, and the bartender can tailor-make your cocktails for whatever is currently showing. The Breaking Bad finale next Sunday 29th? Meth-Tinis. (One can only wonder.) And on Wednesdays — in fact, it kicks off tonight — they host a sci-fi film series, led by science fiction authors.
5. Reserve the “Director’s Chair.” Forget communal dining. Here it’s all about the lounge, and PRIVACY. Especially if you’re fortunate enough to snag the rumored best seat in the house, “The Director’s Table.” And at the “Love Booth,” lovers sit side-by-side, and the high-backs are high enough for no one to bother you (or see what you’re up to). Those are the only two themed seatings, but the lounge is armored with the recipe for a perfect date: dim lighting, the feeling of ultra privacy, and a sprawling, plush sectional in the center.
Henry and Oscar’s is located at 4th Avenue and Vine, and is open every day at 4.
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