Today in ’66: Otis Redding Released the Single That Gave Jon Cryer an Iconic ‘80s Movie Moment

53 years ago today, Otis Redding released the second single from his album COMPLETE & UNBELIEVABLE: THE OTIS REDDING DICTIONARY OF SOUL, and while the song was a decent hit on the Billboard Hot 100, it became the stuff of legend with a little help from the silver screen.

Written by Jimmy Campbell, Reg Connelly, and Harry M. Woods, “Try a Little Tenderness” was first recorded way back in 1932, when the Ray Noble Orchestra released it as a single with Val Rosing on vocals. It would later also be recorded by Bing Crosby and Three Dog Night, but it was a few years prior to the latter’s take on the track that Otis Redding did his version, a.k.a. the one that’s arguably the most iconic of all time.

Various versions of “Try a Little Tenderness” have been featured in a number of films over the years, including Dr. Strangelove and The Commitments, but today we’re focusing on the one that introduced most children of the ‘80s to both the song and the work of Otis Redding.

Yes, that’s right: we’re talking about when Jon Cryer lip-syncs it in Pretty in Pink.

In an interview with The A.V. Club, Cryer offered up the story of how he learned about the song’s selection for that scene in the film and why his unbridled performance caused a schedule change in the film’s production.

“Okay, first of all, I had become fairly well known in my group of friends for doing a somewhat uncanny Mick Jagger impression, so that was my background in lip-synching. We had talked about me doing that, but Howie wanted to do something a little more devotional, something that was a little more about being into someone, because the Rolling Stones’ stuff is often a lot more ironic and detached than that. So Howie’s dad was in the music business for many years and had a lot of connections, and Howie said, ‘What do you think about doing an Otis Redding song?’ And I said, ‘Which one?’ I knew ‘Dock Of The Bay,’ but I didn’t know a lot of his songs. And he said, ‘Well, there’s a song called ‘Try A Little Tenderness.’ I’ll play it for you.’ My first reaction was, ‘This is really long!’ It has this whole long opening that they ended up cutting. But I thought, ‘Okay, this is a different way to go.’ I love the song. I mean, you just can’t listen to that and not be amazed by the song.

“So Howie suggested that I get together with a choreographer, Kenny Ortega, who has gone on to be wildly successful. Actually, he did a lot of iconic dance work in the ’80s; he did Dirty Dancing. So he and I got together one night and came up with some fun stuff to do, but we kept it very loose. And we showed it to Howie the next day, in the actual location, and Howie’s face just fell. And so did Lauren Schuler Donner’s, who was the producer. I’d finished it, and I was huffing and puffing like at the end of Riverdance, my arms outstretched. But they just seemed crestfallen. So I said, ‘What’s the matter?’ And Howie said, ‘Oh, no, it’s great,’ but in this very offhand manner. Then he said, ‘The problem is, I have to shoot it.’ I said, ‘That’s a problem?’ He said, ‘Yeah, because we only slated half a day, and that’s gonna take a couple of days.’ So he and Lauren huddled, and I heard much muttering between the two of ’em, and they agreed to change the schedule. This was in the first week of Howie’s first major gig as a director. So he basically agreed to put himself behind schedule the very first week, thus making him behind the eight ball for the whole rest of the shoot, in order to get that scene. At the time, I didn’t realize that was a really gutsy thing to do. But I think it paid off for the movie.”