Dinner & A Show pays a visit to early-1900s New York City

Soaring skyscrapers, roads bustling with carriages and streetcars — New York City was bursting with growth at the turn of the 20 ^th century.

That history came to life on a recent night out for American Express’ Dinner & A Show series, which pairs Broadway performances with Resy restaurants that match the vibe. We were transported to old-school New York with a feast at Keen’s Steakhouse, established in 1885 and one of the oldest NYC restaurants available on Resy, before settling in for the emotionally gripping Ragtime the Musical, an American Express partner show about the pursuit of the American Dream in early-1900s Manhattan.

As we walked through Keen’s fabled doors, the dark-wood paneled interiors called back to the city’s early architecture. Portraits of historical figures beckoned, the bar echoed a Prohibition-era speakeasy, and 50,000 clay smoking pipes dangling from the ceiling convinced us that 2026 must be decades away.

Just as impressive was Keen’s menu. We sampled a salt-crusted porterhouse, a richly marbled sirloin and Keen’s signature dish: a mutton chop. Seared on the outside and tender and juicy on the inside, it’s a dish that Keen’s has mastered over the past century; just one bite showed why it’s become legendary in the city’s dining scene. A decadent seafood tray, crisp but fluffy hashbrowns, creamed spinach and a butterscotch sundae rounded out our trip back in time.

It was just what we needed before settling in for the second part of the evening: Ragtime the Musical. The show explores the intertwining lives of fictional and historical characters as they chase the American Dream, facing hope and heartbreak, with performances elevated by the late-1800s and early-1900s ragtime music. As part of the “A Night At” series presented by American Express, we also enjoyed a post-show talkback, open to all attendees in the theatre that night. Cast members Joshua Henry, Brandon Uranowitz and Caissie Levy discussed the timelessness present in the theme of the show and the beauty in the writers’ words.

Our night out to Dinner & A Show with Amex and Resy was a reminder that the past isn’t always as far away as it seems.

Book your reservation at Keen’s Steakhouse on Resy, and learn about other theater experiences with Amex.