No matter the decade or the location or the exclusivity of the guest list, the emotions of a wedding day are universal. Alfred Hitchcock looks the classic nervous dad, escorting his daughter, Patricia, to the church. Sly Stone exhibits pure boyish glee as he gets married onstage at Madison Square Garden. Gloria Vanderbilt, truth be told, doesn’t appear all that happy as she sits for a formal portrait, clutching her bouquet in a stranglehold—but that can happen at a wedding. Over the following pages, we take a look back at quintessential New York ceremonies, from the ultrafabulous (Maria Ellington and Nat King Cole at a Harlem church in 1948) to the inventive (Cynthia Rowley and Bill Keenan in an airplane hangar in 1996). As overwhelming and exhausting as it may feel to be a modern-day bride and groom with a wedding to plan, there must be something appealing about the gig or why else would people—including a few featured here—repeat the process over and over again? The answer may be simple: A wedding is a leap of faith. But it’s also a statement of hope, and what better place to make that statement than in the City of Dreams?