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The song, as well as the album on which it is featured, was a marked departure from Chicago's traditional soft rock, horn-driven sound, taking on a polished and modern feel. With minimal horns, the track instead featured more layered synthesizers and heavier distorted guitar in a contemporary 1980s styling. This was done to revitalize the band's commercial success
Deviating from Chicago's practice of having mostly band members playing on their albums, "Hard to Say I'm Sorry" featured several session musicians. The song featured producer David Foster on the piano, as well as three members of the American rock band Toto, including Steve Lukather on guitar and David Paich and Steve Porcaro both contributing synthesizers. The song's vocals were performed by Peter Cetera. The only other member of Chicago besides Cetera that played on the track was drummer Danny Seraphine.
Chicago made a music video for the song. According to Cetera, the videos for "Hard to Say I'm Sorry" and "Love Me Tomorrow" were shot on the same day. The band appears in a black colored room with diamonds on the wall.
In 1996, the R&B group Az Yet included a cover version on their self-titled debut album. The song, later released as a single, was produced by Babyface, remixed by David Foster, featured vocals from Peter Cetera, and peaked at number eight on the Billboard Hot 100. The single reached platinum status and was nominated for a Grammy Award for Best Performance by an R&B Group or Duo with Vocal.
"Hard To Say I'm Sorry" (David Foster Remix Featuring Peter Cetera) 3:18
*sales figures based on certification alone ^shipments figures based on certification alone
Other cover versions
In 2003, the Canadian boy bandb4-4 recorded a cover version included as a bonus track on the "limited edition" of their second album In Your Face.
In 2007, Irish boy band Westlife covered the song on the B-side to their single "Home" from the band's seventh UK #1 album Back Home. The song charted itself without being properly released as a single.
In 2015, country music star Tim McGraw released a "behind-the-scenes" video of him and his band performing "Hard to Say I'm Sorry" as a warm-up for his show in Chicago. At the end of the song he turns to the camera and says, "Hello, Chicago."
After interviewing Peter Cetera while he was in Lucerne, Switzerland to perform at the Retro Festival in 2016, Swiss interviewer and musician, Phil Dankner, performed the song for Cetera.