Photos by Andy Argyrakis

For a guy with 11 number one hits to his name plus a pool of gold and platinum albums, Freddie Jackson sure doesn’t get to town nearly as often as he should. With that in mind, the crooner and sometimes songwriter had no trouble selling out the up close and personal City Winery, but rather than focusing on material from his reemergence in the 2010s, dipped back to all of his most beloved quiet storm singles from the ‘80s and ‘90s.

Those sitting on the left side of the stage also let out some extra yelps during “You Are My Lady” thanks to a marriage proposal, which mirrored Jackson’s introduction of the dusty now belonging exclusively to the fans following 31 years of performances (and 26 weeks atop the charts during its initial run).

Looking extremely slender coming direct from an engagement in Spain, Jackson was smooth and sultry personified as he entered to the beats of “Nice ‘N’ Slow” with longtime admirers and even actor/comedian Chris Tucker cheering him on. For the next 75 minutes, that velvety voice may have been the primary star of the show, but a six-piece band and pair of background singers added just the right touches of supplementary soulfulness and jazzy elegance.

Whether it was “Do Me Again,” “Jam Tonight,” “Love Is Just A Touch Away,” “I Don’t Want To Lose Your Love” or “Rock Me Tonight (For Old Times Sake),” the ladies repeatedly lost their minds and screamed for more. Those sitting on the left side of the stage also let out some extra yelps during “You Are My Lady” thanks to a marriage proposal, which mirrored Jackson’s introduction of the dusty now belonging exclusively to the fans following 31 years of performances (and 26 weeks atop the charts during its initial run).

Outside of his own material, the headliner also broke into some gospel with Kirk Franklin’s “Why We Sing” and offered additional snippets or references to Marvin Gaye, Johnny Mathis, The Temptations and Teddy Pendergrass. He ended with “Hey Lover,” perhaps the quintessential summary of those many legendary influences, while also invoking a sense of timelessness that continues to tie together his decorated catalogue.

Click here for more Freddie Jackson photos from City Winery

For additional information on Freddie Jackson, visit FreddieJackson.net.

Upcoming concert highlights at City Winery include (Jan. 13); Chicago Philharmonic Brunch (Jan. 15); RES (Jan. 15); Kris Kristofferson (Jan. 16-18); Hot Club of Cowtown (Jan. 19); Kevin Griffin (Jan. 20-21); A Muscle Shoals Revue with The Amy Black Band (Jan. 22); Josh Ritter (Jan. 22-23); Steve Earle (Jan. 24-25); Alejandro Escovedo (Jan. 26-28); Louie Anderson (Jan. 29) and Luke Wade (Jan. 31). For additional details, visit CityWinery.com/Chicago.

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