“You know, you can wait around and hope, but you’ll never see the likes of this again.” Those words came from Frank Sinatra in the 1974 film That’s Entertainment!, a compilation as self-serving as it is delightful. The two-hour document of all things MGM musicals featured a number of stars who had prominently featured in the studio’s best-known style of filmmaking, including Sinatra, Gene Kelly, Fred Astaire, and more. Sinatra said that line in reference to the jaw-dropping “Begin the Beguine” number with Astaire and Eleanor Powell, in fairness, but it could just as easily apply to another song featured in the film.
That song is “Well, Did You Evah?,” from the 1956 musical High Society, which turns 70 today. But if Sinatra had been talking about “Well, Did You Evah?,” he’d have been talking about himself, as it’s a Cole Porter duet performed by him and another musical icon, Bing Crosby. The film is perhaps not the finest of the MGM musicals, but this song is cinematically akin to De Niro and Pacino facing off in Michael Mann’s Heat: two legends going toe to toe on the big screen for at least one brief moment.
High Society, a musical adaptation of the same play that inspired the 1940 screwball classic The Philadelphia Story, is more well-known for a few of its numbers and extratextual details than the film as a whole. Sinatra and Crosby are two-thirds of a love triangle, completed by the luminous Grace Kelly in what would be her final film role before her marriage and ascendancy as the Princess of Monaco. The three fit into the primary roles in The Philadelphia Story, with Sinatra as journalist Mike Connor, Crosby as C.K. Dexter Haven, and Kelly as Tracy Samantha Lord, taking over for James Stewart, Cary Grant, and Katharine Hepburn, respectively. There are tweaks that fit the new actors, such as Crosby’s Dexter Haven being a jazz singer instead of a yacht designer, but the storyline is broadly similar, just with music.
Though Porter wrote the songs in High Society, some were written for earlier shows. “Well, Did You Evah?” is one such case, originally appearing in his Du Barry was a Lady. (The 1943 film adaptation of that show, also from MGM and co-starring Kelly and a young Lucille Ball, only featured the song partially in an early medley.) Within High Society, the song functions as a duet between the two men vying for Tracy’s affections, but it also existed as a larger-than-life combination of two generationally separate crooners. It’s not quite the same as a much older Bing doing a Christmastime duet with the young David Bowie, but getting Crosby and Sinatra together for the first time feels major, transcending the sly and slightly soused lyrics.

When you actually watch “Well, Did You Evah?,” you see two men on different trajectories of their career. Crosby, the Oscar-winning actor and singer associated with the holiday season, was nearing the end of his big-screen life. (One of his final roles was in another film with Sinatra, Robin and the 7 Hoods. That time, he was the support while Sinatra was the lead.) Sinatra, meanwhile, had become one of the biggest names in film and music, and his own legendary status would expand greatly in the decades to come. Here, he’s still paying fealty to an icon in his own right.
Though Porter rewrote the lyrics for the film, the general idea of “Well, Did You Evah?” is still the same: two people riffing on various attendees of a swanky gala with insouciant wit. There’s something akin to fourth-wall-breaking near the end of one of the verses, as Dexter Haven does some basso scatting (as Crosby often did), Mike quickly retorts “Don’t dig that kind of croonin’, chum,” and is met with the deadpan line, “You must be one of the newer fellas.” But what comes across most of all in the three-and-a-halfminute clip is both men’s dry humor and delivery, and their undeniable charisma, not just playful winking at the audience.
High Society was not the last of the MGM musicals, arriving in theaters two years before eventual Best Picture winner Gigi. But the 1956 film was one of the last major gasps of the studio’s pioneering genre, as some splashier 1960s-era big-screen musicals wound up being adaptations of stage shows like The Sound of Music and My Fair Lady. This film’s claims to fame are as ostensible footnotes in their stars’ careers, or as the delivery unit for a rousing Louis Armstrong musical number called “Now You Has Jazz” as well as the first and most notable instance of two singing icons sharing the screen and getting to duet with each other. “Well, Did You Evah?” is that rare glimpse at two stars standing next to each other, big smiles on their faces as they dance their way through a charmingly tossed-off number that was styled to fit each of their personalities and go down smooth.
“High Society” is available for digital rental or purchase.