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Few acts have ballooned in recent years in the way that Post Malone has. On Thursday night, that meant his "Big Ass Stadium Tour" made its way to Chicago, where it was welcomed by a big crowd at Wrigley Field. Here's nine reasons why you should have made the drive down:
1. He Poured Us a Drink,Like a True Wisconsinite at Heart
Post Malone didn’t just sing about drinking,he lived it, red solo cup in hand,
with the energy of someone tailgating outside Lambeau in subzero temps.
Whether it was whiskey-soaked heartbreak or beer-fueled singalongs, his love
for a good drink felt almost Midwestern. Honestly, swap his cowboy hat for a
Brewers cap, and he could’ve passed for a local. While Chicago technically
hosted the party, the vibes were pure Wisconsin.
2. No Milwaukee? AmFam Field South Will Do for a Night
It hurt a little that Milwaukee didn’t make the tour schedule, but Brewers fans
have a long tradition of turning Wrigley Field into "AmFam Field South"
anyway, and Thursday night was no exception. From the parking lot tailgates
to the sea of fans who made the I-94 trek, it felt less like enemy territory and
more like a road game takeover. Sure, the ivy was still on the walls, but the
energy? That was pure Milwaukee.
3. The Setlist Spanned a Genre-Bending Decade of Bangers
Only Post Malone can play a pedal steel-driven tearjerker and follow it with a fireball anthem like "rockstar." He zigzagged through his discography like a drunk Uber driver, and the crowd loved every swerve. "Better Now," "Circles," "Psycho," and "Congratulations" hit just as hard as newer cuts like “Pour Me a Drink” and “I Had Some Help.”
4. It Was a Perfect Night for Fans of All Genres
Posty may have gone full country with "F-1 Trillion," but the show was far from genre-exclusive. His setlist was a buffet of his musical eras, from early trap ballads like “White Iverson” and “Go Flex,” to pop mega-hits like “Sunflower,” to his new honky-tonk heartbreakers. Whether you came for the cowboy twang, the Auto-Tuned crooning, or the radio-ready bops, there was something for everyone.
5. Posty’s “Congratulations” Had a Firework Finale Worth a Fourth of July
Post Malone doesn’t end shows, he launches them into the stratosphere. The closing combo of “Sunflower” and “Congratulations” came with a full-on fireworks show that lit up the Chicago skyline. It was over-the-top, chaotic, and totally earned. If the Cubs ever win another World Series, they’d be lucky to get half that show.
6. He's Only Getting Bigger
If you saw Post Malone during his last Wisconsin-area stop at Alpine Valley Music Theater, you know he’s always been a great live act. But this show proved just how fast he’s leveling up. The visuals, the pyro, the stage presence—everything was turned up. He’s gone from theaters to ballparks, and soon, tickets will be even harder to come by. This was the kind of tour people will brag about having seen when he's selling out stadiums overseas or headlining festivals solo.
7. Jelly Roll's Opening Set Was Worth the Drive Alone
Jelly Roll didn’t just open the show, he nearly stole it. His gritty, heartfelt set bridged the gap between southern rock and hip-hop gospel, and by the time he joined Post onstage for their duet “Losers,” it felt like two old friends closing out the night at a dive bar. Their post-song hug? The emotional peak. Even Chicago Cubs fans had tears.
8. Post and Jelly Roll Together Are Our Favorite Face-Tatted Bromance
Some collabs feel like business deals. This one felt like a backyard barbecue. Their chemistry on “Losers” was undeniable, with Jelly’s soulful grit blending perfectly with Post’s raspy twang. And when Sierra Ferrell joined for a pedal steel moment on "Never Love You Again," it wasn’t just a performance,it was a genre-defying celebration of friendship, music, and every misfit who's ever found a home in a song.
9. Jelly Roll Brought Out Some Big Guests
As if Jelly Roll’s set wasn’t already packed with grit, heart, and Southern soul, he kept the crowd guessing with surprise appearances that gave the night an extra edge. First, he brought out Alex Warren (who you can catch at Summerfest this year) to perform their new single “Bloodlines”. Then later, in true curveball fashion, Jelly Roll welcomed comedian Bert Kreischer (yes, shirtless of course) to the stage, turning the vibe from heartfelt to hilarious. It was chaotic in the best way possible and proved that when Jelly’s involved, anything can happen.
