2 Cowboys Give Killer Cover Of ‘Back When I Knew It All’

YouTube/Steve Woolsey Music

Jamming out on stage, these two singing cowboys show everyone what they’re made of when they sing one of the biggest Montgomery Gentry hits ever released! 

Steve Woolsey and Trent Willmon both appear onstage with guitars and microphones, but nobody was expecting the incredible jam session that erupted when these two powerhouse musicians got together! 

Willmon, who actually co-wrote the song, has had his own success on country radio after releasing several singles – and what a sound he gives to this unforgettable hit! 

Debuting in February 2008 as the title track to their album, Montgomery Gentry’s “Back When I Knew It All” stole the hearts of country listeners everywhere and soared to the No. 1 chart position.

This stunning songwriter jam session took place in Wellsville, NY just a year after this song debuted and the crowed loved their killer rendition.

Check the video out below!  

Save this article!
Get this sent to your inbox, plus get new articles & videos from us every week!
Please enable JavaScript in your browser to complete this form.

About the Author

Manly Bryant

Throughout his over a decade-long career at Country Rebel, Manly Bryant has written thousands of articles, managed countless social media posts, connected with many country music stars in person, and documented many of the most iconic moments in country music history. Whether he’s covering a sold-out stadium show or spotlighting an up-and-coming artist, Manly brings…

This post may contain affiliate links. Please read our disclosure policy.