If you think it's an unlikely collaboration, well that's the point - the brand wants to "close the gap between us." Cher and Future both feature in a video where they perform a duet of Everyday People originally by Sly and the Family Stone, adding a modern hip-hop trap sound.
"I love the idea of 'Meet Me in the Gap' because it's easy to have common ground if you are really open and curious to people from different cultures," said Cher. "I didn't know who Future was before this but I knew it would be so fun to work with someone who is completely unlike me, and who is young, really talented and striving."
This isn't Cher's first fashion campaign - in 2015, she was hired to star in Marc Jacobs' autumn/winter adverts.
The campaign sees Cher wearing a Gap denim jacket over one of her trademark bejewelled sheer showgirl looks, while Future is pictured in a leather jacket, sunglasses and a classic white V-neck.
"As a brand, our heritage is rooted in being a beacon of hope and optimism while also bringing people together," said Gap chief marketing officer Craig Brommers. "Uniting two superstars like Cher and Future proves that no matter how different we seem, there is always a common thread that we just might not have discovered yet."
Earlier this year, Gap made a strong bid to revive its ailing fortunes after launching an archive collection that harnessed its original 90s cool. Starring Naomi Campbell, the campaign also featured the children of previous advert stars Rumer Willis, Lizzy Jagger, Diana Ross' son Evan, Run DMC's son, TJ Mizell and Stephen Tyler's daughter, Chelsea.