No one's a better Midtown Manhattan guide than Jim Caruso. He is the ultimate figure at Birdland, a historic jazz club in the center of the neighborhood, where you’ll find him hosting his open mic night: Jim Caruso’s Cast Party. Every Monday for the past 18 years, he’s been here taking the stage with the city’s most talented (and eccentric!) characters.
Sometimes Caruso is in the spotlight. He’s both a cabaret performer and a jazz singer, and he also appeared in Liza Minnelli’s Tony Award-winning Broadway show, Liza’s At the Palace. These days you’ll most likely catch him at Birdland, yes, but also belting out songs late into the night at Bemelmans Bar at The Carlyle Hotel.
Most people know that the TKTS booth is the place to buy discounted same-day Broadway tickets. While you probably won’t be able to snatch front-row seats to Hamilton, you will have a wide choice of top-rated productions. (It’s hard to go wrong on Broadway!)
While the main ticket booth is in Times Square, Caruso recommends avoiding the crowds and instead heading to the TKTS booths in the South Street Seaport area or across the street from Lincoln Center. “The Times Square booth usually has an endless line, so if you’re anxious like me, a quick cab ride to the Lincoln Center booth will be just the ticket,” he says.
It’s difficult to walk a block in Midtown without running into a pizza joint, most of which claim to be “famous” in some way. But Caruso has a favorite secret gem: B Side Pizza and Wine Bar. It’s located at Ninth Avenue and 51st Street, a few blocks from the chaos of Times Square, so you’ll run into way more locals than tourists. It’s cozy, rustic, and low-key, so you can go there on a date or with your entire family.
“More important, it has some of the greatest artisanal pizzas this side of Palermo,” Caruso says. “Historically, I have turned up my nose to any pizza that involved fruit, but I still have happy dreams about the Don Ho pizza, loaded with tomato, roasted pineapple, prosciutto, burrata, and pickled fresno chiles.”
The crowds are part of the fun in this part of Manhattan. There are few other places where you can bump into people from all over the world taking pictures and gawking at lights. But when you need a break, Caruso suggests heading to the Lobby Bar inside Ian Schrager’s recently opened Times Square Edition Hotel.
Set on Seventh Avenue, the lounge is both stylish and zen with all-white furniture and sexy lighting. “It’s a respite from the insanity,” Caruso says. “Being there is a vacation for your eyeballs.” He recommends indulging in the ice cream sundae made with dulce de leche and toasted peanuts.
If you want to hobnob with New York City’s Broadway stars, Joe Allen is your spot. “Insiders know that all the show posters on the walls represent notorious flops,” he said. “It’s a rite of passage to make it to those walls, and I’ve had my share of dinners with friends who are represented.”
This tavern-like bar first attracted Broadway stars in 1965 when it offered 75-cent hamburgers and all the American comfort food (from grilled New York strips to jumbo crab cakes) any hungry actor could want. Now, it’s still a hot spot for performers as well as their fans. “Sometimes it’s all I can think about during the show,” Caruso says. “Which isn’t particularly a compliment to the show.” It’s open until just before midnight every night of the week.
While most tourists stick to Times Square and the Theater District, Caruso wants visitors who are walking around or people watching to know the neighborhood is much larger. In fact, many of the treasures are outside of those heavily populated areas.
“There are so many wonderful restaurants, bars, and clubs that are a bit off the beaten path,” he says. “If you venture one or two blocks east or west of Times Square, you’ll be able to see honest-to-goodness New Yorkers eating and drinking! Look at them wearing black and being sarcastic! Aren’t they fun?”
When Caruso has friends and family members visiting, he takes them to Fine and Dandy, a tiny accessories boutique on West 49th Street in Hell’s Kitchen.
“They have ties, pocket squares, scarves, hats, tie bars, cummerbunds, cufflinks, belts, even spats,” he says. “Yes, it’s old school, but I’ve seen some of the hippest folks in town swooning over the inventory.” Whether you’re shopping for yourself or a loved one, you’ll leave with an original gift.
Caruso knows that Times Square is a must see for any visitor. While there, he insists you make it to the club where he works. “What kind of a New Yorker would I be if I weren’t self-aggrandizing?” he says. “You have to come to Birdland! It’s a block away from the insanity of Times Square, but once through the doors, you’ll forget the mobs, the Naked Cowboy, and the grody Elmo.”
The historical club does have a lot going for it. It opened in December 1949 and has attracted the best singers since. One night you might hear a soloist. The next, a jazz band or Broadway diva. Also, the food and drink are well-priced for the area. Have a drink (or two or three) while watching the stars perform (and your New York City expert work the room).