The New York City appearance was part of Cross’ latest tour marking the 40th anniversary of his self-titled debut album. Originally released in 1979, the multiplatinum Christopher Cross catapulted the then-unknown Texas singer-songwriter to fame. Not only did it generate such popular soft rock singles as “Ride Like the Wind,” “Sailing,” and “Never Be the Same,” but the album alone netted Cross four major Grammy Awards: Album of the Year, Record of the Year (“Sailing”), Song of the Year (“Sailing”) and Best New Artist—an accomplishment later repeated by Billie Eilish in 2020.

More than just honoring the legacy of Cross’ first album, the show was also a celebration of Cross’ four-decade career as well as a testament to his perseverance and survival following a major health scare: he had a serious bout with COVID in 2020 and was later diagnosed with Guillain-Barre Syndrome, a condition, per the CDC, in which the immune system attacks the nerves causing weakness and possibly paralysis.

Amid a large backdrop featuring an illustration of a pink flamingo that hearkened back to the cover art of Christopher Cross, the singer and his band performed the first album in its entirety, including such deep cuts as “Spinning,” “Poor Shirley” and “The Light Is On.”

Other songs from the early and latter parts of his career were sprinkled in the set, among them “All Right,” “No Time to Talk” and “Swept Away.” Cross’ band also performed a short snippet of the Dave Brubeck Quartet’s classic “Take Five,” related to a story the musician told about his childhood and early introduction to music.

The main set concluded with a rollicking and exuberant rendition of “Ride Like the Wind” that got the audience moving and rocking out. For the encore, accompanied only by his keyboardist, Cross performed the tender and sublime ballad “Think of Laura,” which originally appeared on his 1983 album Another Page.

Along with the music of Michael McDonald, Kenny Loggins, Hall and Oates, and others from the yacht rock era, Cross’s career has undergone renewed appreciation by later generations of music fans. The City Winery show was a solid overview of a career that showcased Cross’ growth as an artist beyond the success of his first album—proof that his music still connects with listeners both old and young.

Setlist (based on previous shows from the tour):

Minstrel Gigolo

All Right

Never Be the Same

Take Five (Dave Brubeck Quartet cover)

I Really Don’t Know Anymore

Poor Shirley

Sailing

Walking in Avalon

Dreamers

Arthur’s Theme (Best That You Can Do)

Swept Away

Say You’ll Be Mine

Spinning

The Light Is On

No Time for Talk

Ride Like the Wind

Encore:

Think of Laura