Duncan Trussell at Pittsburgh Improv – Pittsburgh, PA

See Struggle Jennings Live in Milwaukee on Tuesday, March 24, 2026, Doors Open at 8:00 PM

Struggle Jennings was destined to be an OutlawThe grandson of legendary Country Music icon Waylon Jennings, Struggle is part of a long legacy of Gangsters, Outlaws and Rock Stars.. Growing up as a black-sheep in his family, he fought his way out of the streets of West Nashville and into the studio where he would create the foundation for what has become his personal contribution to the Jennings family legacy..Struggles message of strength, determination, and courage in the face of adversity continues to connect and resonate with people around the world. By sharing his story with honesty and passion he has developed a large and loyal fanbase who relate not only to his music but also to his personal journey.Since being released from prison in 2016 Struggle has performed for sold out crowds across the country and released multiple projects. He is finally poised to take his place as a true modern day Outlaw and secure his position as the Godfather of the burgeoning Outlaw Hip Hop Rock & Roll movement.

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Planning to attend an event at Shank Hall

Here’s what all Struggle Jennings fans must know before attending an event at Shank Hall. To ensure a stress-free experience, we recommend arriving at the venue at least 45 to 60 minutes prior to the scheduled start time. This allows ample time for navigating local Milwaukee traffic, securing parking, standing in long wait lines and passing through venue security.

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