Brendan Bayliss and Jake Cinninger got fans in the holiday spirit on Saturday with the 20th edition of their annual Holiday Show at The Park West in Chicago, IL. The dynamic duo was joined by Umphrey’s McGee percussionist Andy Farag and pedal steel player Mike Racky for an acoustic evening of UM originals (including the debut of “How About Now” from the new album Asking for a Friend), covers, and holiday classics. Annie Bayliss would lend her vocals on a cover of The Pogues’ “Tales of New York”, giving the show a family-friendly, holiday feel.

Hosted by Barry Brown, the proceeds raised during the evening from ticket sales, basket raffles, and more benefitted The People’s Music School, a free music school serving Chicago metropolitan area children.

Related: UPDATE: Umphrey’s McGee Extends ‘umXXV’ 25th Anniversary Tour With Nine New Dates

Check out a gallery of images from Brendan & Jake’s 20th annual Holiday Show at The Park West courtesy of Sara Jachimiak. On-demand video of the event is available until December 26th on

Brendan Bayliss & Jake Cinninger – The Park West – Chicago, IL – 12/10/22 – Preview

Brendan Bayliss & Jake Cinninger – “Too Late for Goodbyes” (Julian Lennon) [Pro-Shot] – 12/10/22

Brendan Bayliss & Jake Cinninger – “Fairy Tale of New York” (The Pogues) – 12/10/22

[Video: Kevin Higley]

Setlist: Brendan Bayliss & Jake Cinninger | The Park West | Chicago, IL | 12/10/22

Set: Remind Me > Half-Delayed, August > It’s Not Your Fault > August, Nemo^ > Wife Soup^ > Nemo^, Bad Poker^*%~ > Cut The Cable^*, Always October^, Dayville Monarchy^, Gulf Stream^*, Dreams (Fleetwood Mac)^*, You and You Alone^*, How About Now ^*, In Bloom (Nirvana)^*€, Little Drummer Boy ^*, Hajimemashite^*, Susannah (30db)^*+, Too Late For Goodbyes (Julian Lennon)^*

Encore: Champagne Supernova (Oasis) ^*, Baker Street^*$, Fairy Tale of New York (The Pogues)^*£

^ Andy Farag
* Mike Racky
+ Barry Brown
£ Annie Bayliss
% Sweet Home Alabama tease
~ Carol of the Bells tease
€ Sturgill Simpson cover version
$ Brendan on Kazoo