Photos by Andy Argyrakis

At the tail end of the CD era, singer/songwriter/piano player Vanessa Carlton was selling them by the millions and etching her place in pop culture, thanks in part to the beautiful ballad “A Thousand Miles.”

She’s been regularly recording and touring the entire time, trading major label life for total artistic freedom, while continuing to amass a dedicated fan base, who quickly sold out a pair of shows on the “Future Pain” Tour at the acoustically satisfying City Winery.

Hopefully, those who came with the primary purpose of hearing that aforementioned hit were punctual for the first performance because it was indeed Carlton’s unexpected but still exceptional opener, suggesting the troubadour was eager to update everyone on more recent whereabouts.

And to quote the title of a newer tune, “I Can’t Stay The Same,” Carlton appeared to be evolving even further from a brighter, pop-flavored past into a more introspective, experimental and ambitious indie pop/rock direction, in additional to a starring in Broadway’s “Beautiful” and temporarily becoming a substitute teacher during COVID.

Regardless of the changes, her inviting vocals, instrumental aptitude and thought-provoking lyrics were as engaging as ever throughout “Willows,” the Stevie Nicks-covered “Carousel” and “Back To Life,” plus she intermingled other earlier singles, such as “Ordinary Day” and the complete “White Houses,” laughing off what was once inexplicably censored by MTV.

This 80-minute visit also included the haunting likes of “House Of Seven Swords” and the health-focused “Hear The Bells,” which were further amplified by the abundant talents of cello/electric bass player Isabel Castellvi.

Though Carlton stayed seated since she was nursing a broken foot, an implied encore segment started with “Who’s To Say,” dedicated to the entire LGBT community, especially in light of Tennessee’s anti-drag insanity, and ended with “Love Is An Art,” the title track to her latest long player, unfortunately released at the pandemic’s onset.

Toss it all together, and it’s certainly worth a shot to sign up for the City Winery waiting list should something open up on Wednesday, March 15, just make sure to arrive early in case Carlton once again opens with a defining millennial moment and stay for the classics to come.

For additional information on Vanessa Carlton, visit VanessaCarlton.com.

Upcoming concert highlights at City Winery include Vanessa Carlton (Mar. 15); Rumor Has It – Adele Tribute (Mar. 16); Zach Heckendorf (Mar. 17); Obisoulstar (Mar. 18); Gilbert O’Sullivan (Mar. 19); Nicholas Tremulis & The Prodigals (Mar. 20); Oz Noy & Ozone Squeeze (Mar. 21); Peter Mulvey & Sistastrings (Mar. 22); EXTC (Mar. 23); Krasno/Moore Project (Mar. 24); The Verve Pipe (Mar. 25); Chris Fairbanks (Mar. 26); Ilysm (Mar. 27); J. Ivy (Mar. 28); Aniba & The Sol Starz (Mar. 29); Boy and Review (Mar. 30); Pure Prairie League (Mar. 31); Freddy Jones Band (Apr. 1); Wayne Baker Brooks (Apr. 2); Attack The Sound (Apr. 3); One Of These Nights – Eagles Tribute (Apr. 4); Jamo Laurice (Apr. 5); Smells Like Nirvana (Apr. 6); Keith Washington (Apr. 7); Babealon 5 (Apr. 8); Dwele (Apr. 8); Tim Woodson & The Heirs Of Harmony Gospel Brunch (Apr. 9) and George Willborn (Apr. 9). For additional details, visit CityWinery.com/Chicago.

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