Photos by Andy Argyrakis

When malls were the only way to social network, Tiffany was the queen of food court concerts, though the 1980s’ equivalent of Ariana Grande packed just as much vocal and songwriting substance as she did sugary pop.

Those qualities especially became apparent when she branched out into rock and country terrain on record throughout the ‘90s and 2000s or anytime she’s on a stage nowadays, such as the City Winery, where she was easily the most prominent post-lockdown performer (at 15-times platinum!) to tour through Chicagoland thus far.

Throughout the entire reopening process, the venue’s been taking all the necessary steps to ensure attendee safety, including socially distanced shows, no shared tables between unaffiliated parties and online ordering, which coupled with their already first-rate environment, makes this a premiere spot to get settled back into the live scene.

Even Tiffany remarked how wonderful it was to be back in such a pitch perfect room as she knocked out several homeruns dating back to a record-setting, eponymous debut that made her Billboard’s youngest female chart-topper, through an album slated for October release, “Shadows,” which is being produced by Mark Alberici in Wales.

Along with a four-piece band, including L.A. Guns recruits Johnny Martin and Scot Coogan as the rhythm section, the brand new “Hey Baby” gave a punked-up wink to her bubblegum origins, while “Beautiful,” “King Of Lies” and “Feels Like A Storm” (all from her previous project “Pieces Of Me”) were noticeably kicked up a notch.

The #1 ballad “Could’ve Been” was perhaps the ideal vehicle to showcase Tiffany’s pipes, particularly in the intimacy of this classy club as compared to the arenas she played alongside New Kids On The Block, Salt-N-Pepa, Debbie Gibson and Naughty By Nature on the “Mixtape” Tour to over 600,000 fans.

As is customary, the hit maker flipped the gender of The Beatles’ “I Saw Him Standing There” to winning results, followed by the raw emotion of the upcoming “Bed Of Nails” and Rival Sons’ rowdy plea for resilience, “Keep On Swinging.”

Fellow chart-topper, “I Think We’re Alone Now,” was an obvious but welcome finale, and while her version came between those by Tommy James & The Shondells and Green Day’s Billie Joe Armstrong, Tiffany’s take is arguably paramount in the annals of pop culture.

While it was a delight to have this particular star back in town, if only for a double-decker night, the fact that City Winery is serving up a full calendar (and menu) gives the Windy City a load to look forward to in this bizarre, better late than never summer of shows.

Click here for more photos of Tiffany at City Winery.

For additional information on Tiffany, visit TiffanyTunes.com.

Upcoming concert highlights at City Winery include Kick The Cat featuring Kris Myers of Umphrey’s McGee (Jun. 22); The Docksiders (Jun. 23); Journeyman: A Tribute To Eric Clapton with Dina Bach (Jun. 24-25); Armchair Boogie (Jun. 27); Chrisette Michele (Jul. 2); Naturally 7 (Jul. 3); Deacon Blues: The All-Star Tribute To Steely Dan (Jul. 7); Howard Hewett of Shalamar (Jul. 8); The Verve Pipe (Jul. 10) and Rhett Miller (Jul. 11). For additional details, visit CityWinery.com/Chicago.

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