Daryl Hall wrote this for his collaborator/girlfriend Sara Allen. Her sister, Janna Allen, co-wrote their hit "Kiss On My List." Janna died of leukemia in 1993. (thanks, Charles - Charlotte, NC)
They never got married, but Daryl and Sara were together for about 28 years before they broke up in 2001. In Entertainment Weekly October 16, 2009, Hall listed this as one of their favorite songs, and explained: "That was a postcard to Sara Allen, who was my partner for many, many years, a 'having a great time, wish you were here' kind of thing. I cannot tell you how many girls have told me they were named for it!"
The album's cover photo by Mick Jagger's makeup designer Pierre LaRoche is a glitzy shot of Hall and Oates in heavy makeup. John Oates talked about the eye-catching image in Nick Tosches' biography Dangerous Dances
: "We decided that if we were going to put our faces on an album cover for the first time we wanted to do it in a big way. Pierre said, in that French accent of his, 'I will immortalize you!' And he just did. To this day it's the only album cover that people ask us about."
David Bowie said that LaRoche was the best makeup artist he ever worked with.
According to Barry Rudolph, who was an engineer on the session, Hall sang his vocal live with the band. The only edit they made was to punch in over the word "Sara" in the beginning of the second chorus. With the backing vocals, Hall was trying to get them to sound like the Doo-Wop group The Dells.
In 2009 country singer Jimmy Wayne recorded an updated version of this song with Hall and Oates. Wayne got his first record deal because of this tune after then-Dreamworks executive Scott Borchetta heard him sing it and it has been part of his concert repertoire ever since. Wayne said in publicity materials: "Over 13 years ago, I picked a Hall & Oates Greatest Hits CD out of a bargain box that sat outside the department store in the old Gaston Mall in Gastonia, North Carolina. I listened to the CD on my way home and I heard 'Sara Smile' for the first time. I began singing this song long before I knew how to play it on guitar and I just felt like it was as if the song was written for me."
The Jimmy Wayne updated version was Hall and Oates debut on the Hot Country Songs chart.
This song was performed on the episode "Tom, Sarah and Usher" of the Adult Swim show The Boondocks. In the episode, Tom DuBois started to sing the song to his wife, when Usher comes in and sings the song a lot better. (thanks, Logan - Troy, MT)
Tommy Mottola, who would later become chairman of Sony Music and marry Mariah Carey, was Hall & Oates manager at the time. He had some experience as a musician (recording as "T.D. Valentine"), and is credited for playing keyboards on the Daryl Hall And John Oates album.
Chris Bond produced this track with Hall & Oates. According to Scott Edwards, who played bass on this song, much of its success is attributable to Bond. Says Edwards: "Chris Bond was the real impetus behind 'Sara Smile,' 'Rich Girl,' 'She's Gone' for Hall & Oates. But he was never given the accolades he deserved. He's the one in my mind that was really responsible for their success. They may have written the lyrics and the chords and all that, but Chris was the one who figured out the production and the projection of it. He was a really good arranger and he wrote out note for note. He knew exactly how long he wanted you to let a note ring, how to hit it, how to release it. He was a good guitar player, but he played all the instruments. So he was one person who really could write out everything and it would be great." (Here's our full Scott Edwards interview
As you can imagine, this is a tough song for Sara Allen to hear, and since it still shows up on many playlists she can't always avoid it. Daryl Hall explained to American Songwriter: "When that song comes on, the reality hits that we're not together anymore, so it's a very poignant and hard thing for her to deal with. I can still sing that song today and feel real about it - and always will - because emotions don't change even though circumstances change."