Christopher Cross Goes ‘Sailing’ on ‘Jimmy Kimmel Live’: Watch

Christopher Cross’ “Sailing” isn’t coming in to dock anytime soon.

The American singer, songwriter and guitar talent released his “yacht rock” masterpiece back in 1979, a classic that sailed all the way to No. 1 on the Billboard Hot 100.

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“Sailing” was one of four top 20 hits that appeared on Cross’ self-titled album, which, in 1981 would make history at the Grammy Awards, by sweeping five categories, including the Big Four — album, record and song of the year. Yes, it was unexpected. A shock, even. The only other artists to scoop the Big Four was Billie Eilish, doing so four decades later, in 2020.

If “Sailing” was a guilty pleasure in the 1990s, today it’s simply a pleasure. The softly-spoken artist stopped by Jimmy Kimmel Live earlier this week to take us all “Sailing,” the video of which can be seen below.

Cross, a formidable guitarist who was blessed with the voice of an angel, appears to have made a full recovery from his grueling health battle five years ago, during which he contracted Guillaine-Barre Syndrome (GBS) after having COVID-19.

At one stage, he was paralyzed from the waist down. “It really was touch and go, and tough,” he CBS Sunday Morning at the time.

Cross’s late-night spot came ahead of the release this Friday, Nov. 14 of All Right: The Worldwide Singles 1980–1988, the first career-spanning collection of his biggest hits, including “Arthur’s Theme (Best That You Can Do),” from the film Arthur, which also led the Billboard Hot 100 and won an Academy Award for best original song. The set is released through Omnivore Recordings, the label that issued an “expanded edition” of Christopher Cross in June 2025.

Now aged 74, Cross will play many of those hits when he embarks on a South American tour this December, including shows with fellow ‘80s heavyweights Toto. Live shows across the U.K. and Europe follow from May 2026.

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