Photos by Andy Argyrakis

To those in Chicago, Michael McDermott is a superb yet criminally underrated troubadour who never got the push he deserved on a national level while getting off the ground in the early 1990s, despite being signed by a series of major labels, plus being heralded as the next Bruce Springsteen or Bob Dylan.

Either of those comparisons are accurate, at least in the lyrical sense, though perhaps best-selling author and longtime fan Stephen King summed him up most accurately as “one of the best songwriters in the world and possibly the greatest undiscovered rock n roll talent of the last 20 years.”

Even so, McDermott broke ground going the independent route in the infancy of the internet and hosted regular livestreams nearly a decade before COVID closures, attracting a dedicated tribe locally and otherwise who are helping make his “Mischief & Mistletoe” residency at the City Winery, continuing Friday, December 21 and Saturday, December 22, one of the hottest holiday tickets.

For those neighbors and travelers from as far as Germany who came to this extra special 50th show at the classy venue, it was not only a festive countdown until Christmas, but a chance to catch up on current projects such as the “St. Paul’s Boulevard” recording and the “Scars From Another Life” memoir, a candid chronicle of substance abuse, financial struggles and musical salvation.

In fact, fresh starts and the sense of healing this season can especially bring were recurring themes throughout two generous hours when the headliner and his longtime band, also featuring fellow solo artist, opener and wife Heather Lynne Horton on violin, provided one life-affirming anthem after the next.

Faithful watched spellbound as he began with many beloved Americana meets roots rock originals, including “Bells” and “20 Miles South Of Nowhere,” alongside a preview of the upcoming “Berlin At Night” as part of a fan-funded Kickstarter campaign.

Fellow sneak peek “Hey La Hey, Number 23,” named in honor of a frequent catchphrase, was dedicated to late 93XRT personality/residency regular Lin Brehmer, while “New Year’s Day” may have come a little early, but certainly fit the ongoing chapter of renewal.

The tone soon turned towards the Yuletide likes of a psychedelically-charged “Little Drummer Boy” and a spunky, funky “Santa Claus Is Coming To Town” as St. Nick himself handed out stocking stuffers to a now-standing City Winery.

McDermott brought it back to his Billboard-buzzing beginnings for “A Wall I Must Climb” and ever so appropriately turned in The Pogues’ “A Fairytale Of New York,” a perennial classic that came across all the more poignantly in the wake of singer Shane MacGowan’s recent passing.

The musical rendition of “Scars From Another Life” further addressed the reflections of a man who finally appears to be at peace after overcoming his demons, but is nonetheless moving forward with the clarity of an accomplished artist capable of belatedly conquering the world.

For additional information on Michael McDermott, visit Michael-McDermott.com.

Upcoming concert highlights at City Winery include Michael McDermott (Dec. 22-23); A Soulful Christmas Brunch (Dec. 24); Raheem DeVaughn (Dec. 26-27); Terisa Griffin (Dec. 28); Raheem DeVaughn (Dec. 29); Rahsaan Patterson (Dec. 30-31); The Purple Madness: A Prince Tribute (Jan. 1); Kindred The Family Soul (Jan. 2-3); Boy Band Review (Jan. 4); The Docksiders (Jan. 5); Pete Correale (Jan. 6); Wayne Baker Brooks (Jan. 7); Jonathan Coulton (Jan. 9); Anthony David (Jan. 10); Scott Thompson (Jan. 11); Dave Hollister (Jan. 12); Maysa (Jan. 13); Midnight Sun (Jan. 14-15); Damon Williams (Jan. 17); The Grateful String Band (Jan. 18); Peach Jam: A Tribute To The Allman Brothers Band (Jan. 19); The Voices (Jan. 20); Jacques Ze Whipper (Jan. 22); Creed Bratton (Jan. 23); Saneit (Jan. 24); Vinyasa & Vino (Jan. 25); Jahari Stampley (Jan. 25); Stephen Kellogg (Jan. 27); Adam Conover (Jan. 28); Midwest Gypsy Swing Fest (Jan. 29); City Of Laughs (Jan. 30) and Denise Thimes: The Best Of Nina Simone & Phyllis Hyman (Jan. 31). For additional details, visit CityWinery.com/Chicago.

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