Watch Steve Winwood & Doobie Brothers Go ‘Takin’ It To The Streets’ In Chicago

UPDATE: Fan-shot footage of Winwood joining The Doobie Brothers on “Listen To The Music” has been added. Watch Steve Winwood’s complete guest appearance below.

Steve Winwood has spent the past month opening for The Doobie Brothers in his first tour of North America in over six years. Last night near Chicago, The Doobie Brothers finally brought out Winwood for their first summer collaboration.

Winwood’s time on the road with The Doobie Brothers began on July 30 in Charlotte and it was surprising they didn’t share the stage over the course of their initial 15 shows together. The rock legends made up for it on Sunday at Tinley Park, Illinois’ Credit Union 1 Amphitheatre, where Steve Winwood emerged for a substantial guest appearance to end the night.

The famed multi-instrumentalist sat at the organ after “Black Water” kicked off the encore. Steve Winwood teamed with The Doobie Brothers’ keyboardist Michael McDonald and saxophonist Marc Russo for an instrumental jam featuring elements of “Amazing Grace.” The piece was used to introduce The Doobie Brothers’ 1976 smash “Takin’ It To The Streets.”

“Takin’ It To The Streets” is the title track to the band’s first studio album to feature Michael McDonald, who returned to The Doobie Brothers in 2021 after a 25-year absence. Michael McDonald shared lead vocal duties with Steve Winwood. The extended rendition included plenty of organ bursts from Winwood and a sax solo by Russo.

Watch Steve Winwood and The Doobie Brothers’ “Takin’ It To The Streets” and “Listen To The Music” performances thanks to audience-captured video below:

https://www.youtube.com/watch?v=xCxZXk21ZSw https://www.youtube.com/watch?v=xhhRUSNIWNU

The Doobie Brothers invited Steve Winwood to “stick around for one more.” A joint version of The Doobie Brothers’ first major hit, “Listen To The Music,” punctuated the concert.

Earlier in the night, Steve’s daughter, Lilly Winwood, joined the headliners on the McDonald-penned gem “It Keeps You Runnin’.” Lilly Winwood first sat in on the song on August 22 in Cuyahoga Falls, Ohio.

The tour pulls into Omaha, Nebraska on Tuesday, August 27. Winwood’s stint supporting The Doobie Brothers ends with shows in Denver on Thursday, August 29 and Salt Lake City on Friday, August 30. Robert Cray then takes over opening duties through the end of the excursion on September 10 in Wheatland, California.