City Winery “Sailing” with a jazzy, self-deprecating Christopher Cross

Photos by Andy Argyrakis

The most famous self-titled album to ever feature a pink flamingo on the cover just turned 40 and was a major reason to catch Christopher Cross kick off a two-night stand at the classy yet comfy City Winery. After all, this is the project that infamously beat out Pink Floyd’s epic “The Wall” for the “Album Of The Year” Grammy, while also swooping up “Record Of The Year,” “Song Of The Year” and “Best New Artist.”

All the vocalists took turns throughout John Lennon’s plea for peace “Imagine” before Christopher Cross docked the sailboat at City Winery overnight in advance of what’s on track to be another pleasant performance.

It’s of course the collection that boasts the exemplary yacht rocker “Sailing,” which was performed third in a two-hour set so Cross could comically penalize any potential latecomers. Not only was the early placement of the track quite a surprise, but so was the singer/songwriter’s self-deprecating sense of humor during conversations with the crowd.

Now 14 studio albums into a prolific catalogue, the headliner teased that several of his less famous works could easily be found at garage sales and flea markets, but despite the lower demand, relatively recent tunes such as the televangelist barb “Reverend Blowhard” and the Joni Mitchell tribute “Roberta” (from his latest offering “Take Me As I Am”) matched the quality of prior radio regulars.

These days, Cross is 67-years-old and seemed to sing in a lower vocal register than he did throughout the 1980s and ‘90s, but a jazzy four-piece band and two smooth background singers more than compensated for any missteps, as did the stories that accompanied many selections. “Arthur’s Theme (Best That You Can Do)” included fond remembrances of working with Dudley Moore and seeing Judy Garland’s original red shoes from “The Wizard Of Oz” at Liza Minnelli’s apartment, while musically “The Light Is On” was a silky, soulful standout and “Minstrel Gigolo” flowed with gorgeous harmonies on top of gentle acoustic strums.

The audience had their chance to sub for Michael McDonald throughout “Ride Like The Wind,” which found a few super fans coaxing others to their feet and calling for an encore that turned out to John Lennon’s “Imagine.” All the vocalists took turns throughout that eternal plea for peace before Cross docked the sailboat at City Winery overnight in advance of what’s on track to be another pleasant performance.

Click here for more photos of Christopher Cross at City Winery.

For additional information on Christopher Cross, ChristopherCross.com.

Upcoming concert highlights at City Winery include Christopher Cross (Mar. 20); The Subdudes (Mar. 21-22); Hip Hop Yoga (Mar. 23; Idan Raichel (Mar. 23); Freddy Jones Band (Mar. 24); Eighth Blackbird (Mar. 25); Van Hunt (Mar. 26); The Tim O’Brien Band (Mar. 27); Robert Glasper Trio (Mar. 28); The Verve Pipe (Mar. 29); Will Downing (Mar. 30-31); Kaitlyn Bristowe (Apr. 1); David Archuleta (Apr. 2); Louis York & The Shindellas (Apr. 3); Tommy Castro & The Painkillers (Apr. 4); Cyrille Aimée (Apr. 5); Willie Nile (Apr. 6); Story Jam (Apr. 7); Tusk (Apr. 7); Miki Howard (Apr. 8-9); Victory Boyd feat. Infinity’s Song (Apr. 10); Downtown Seder (Apr. 11); Martin Sexton (Apr. 12-13); Story Sessions Brunch (Apr. 14); Journeyman: A Tribute To Eric Clapton (Apr. 14); Glenn Jones (Apr. 15); Marc Broussard (Apr. 16-17); Graham Parker (Apr. 18); Carbon Leaf (Apr. 19); Brad Williams (Apr. 20); Dave Davies (Apr. 21); Maggie Speaks (Apr. 22); Liv Warfield (Apr. 23); Rhonda Ross & Rodney Kendrick (Apr. 24); Eric Roberson (Apr. 25-27) and Chicago Philharmonic Sunday Brunch Series (Apr. 28). For additional details, visit CityWinery.com/Chicago.

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City Winery “Sailing” with a jazzy, self-deprecating Christopher Cross

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