Courtesy of The Carlyle, A Rosewood Hotel

It’s Saturday night and the deep voice of indie rock musician Hamilton Leithauser fills the intimate Café Carlyle. Listeners congregate around candlelit tables in small groups. As the audience watches Leithauser’s performance over dessert and cocktails, the vibe feels more like a living room jam session than a formal concert.

Leithauser is part of a new generation of entertainers at the 87-year-old Carlyle Hotel, and he’s crooning in the same space where the late singer and pianist Bobby Short performed for 36 years. Leithauser, like Short before him, makes audience members feel as if they are part of something rare, something special. That intimacy helps explain why the hotel is so dear to so many people, says Matthew Miele, the director of the new film Always at the Carlyle, a documentary debuting on May 8 at the historic Paris Theatre in New York City.

Inside the Gallery Restaurant

Photo by Andrew Moore

“The Carlyle doesn’t feel old,” Miele says. “It feels classic. Paul McCartney and Mick Jagger still come here. Why is it that this place still attracts people like them?” The Carlyle sits on Madison Avenue in New York’s Upper East Side neighborhood. The hotel is where Kate Middleton and Prince William stayed on their first joint trip to the city. It’s where Bill Murray ran amok, singing and dancing with fellow celebrities for his 2015 Netflix special, A Very Murray Christmas. It’s where Alan Cumming spontaneously stripped off all his clothes for the cover of his 2016 album, Alan Cumming Sings Sappy Songs: Live at the Café Carlyle.

Miele started working on Always at the Carlyle in 2014, in collaboration with Rosewood Hotels and Resorts, the Carlyle’s parent company. He interviewed more than 100 people connected to the hotel, including celebrity guests, politicians, housekeepers, concierges, and former general managers. The illustrious cast includes George Clooney, Naomi Campbell, Vera Wang, Roger Federer, and Sofia Coppola.

The Carlyle is known for its discretion.

Courtesy of The Carlyle, A Rosewood Hotel

In the film, Carlyle Restaurant captain Anthony DiLuzio talks about his fascination with the table where Jackie Onassis always sat; Mad Men creator Matthew Weiner waxes poetic about interacting with the ghosts of Tennessee Williams and Mark Twain, both of whom stayed stayed there. And though the hotel prides itself on discretion, Miele does confirm that John F. Kennedy spent time with Marilyn Monroe at the Carlyle. No matter how prominent they are, the hotel strives to put all of its guests at ease. “People say it feels like family here, and it’s true,” says Miele, whose documentaries have also taken behind-the-scenes looks at New York icons Bergdorf Goodman (Scatter My Ashes at Bergdorf’s, 2013) and Tiffany & Co. (Crazy About Tiffany’s, 2016). “When you can walk into a place and say hi to everyone, it makes a difference when choosing where you stay.”

>>Next: Be Our Guest: The Showstopping Hotels That Are Redefining Modern Hospitality

Jennifer Flowers Jennifer Flowers is an award-winning journalist and the senior deputy editor of AFAR.

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