As Wisconsin’s largest city, Milwaukee plays host to its fair share of touring musicians, top-tier comedians, professional athletes, and other pop culture figures of note. That said, it’s also the type of city where the vast majority of those aforementioned entertainers tend to show up, do their job, and move on to the next city. Though some celebrities will publicly declare the mid-market metro to be beneath them, others in the public eye have no trouble going out and having a little too much fun in Milwaukee, which occasionally results in arrests.

While there’s not exactly any need for TMZ to open up a site in town, a handful of famous folks have begrudgingly called Milwaukee an all-too temporary home whilst spending the night (if not longer) in the slammer. Just days removed from the latest such occurrence, we sifted through police records and pulled up some mug shots to find 10 celebrities who did time in Milwaukee.

1. Wes Scantlin (2015)
Last week, news of Wes Scantlin’s arrest and subsequent incarceration surfaced in Milwaukee. Once we all typed “Wes Scantlin” into our preferred search engine, we were struck with the recollection of Puddle Of Mudd’s existence and the shock that the middle-rung radio rockers were still touring. Details—beyond the catch-all charge of “disorderly conduct”—are sparse, but we wouldn’t be shocked if it had something to do with that “She (Fucking) Hates Me” song.

2. George Carlin (1972)
As a whole, Milwaukee is still learning how to be a comedy audience. Stand-up school has apparently been in session for more than 40 years, as legendary comedian George Carlin was arrested after his famed “Seven Words You Can Never Say On Television” bit upset the delicate sensibilities of an off-duty police officer who happened upon the comic’s Summerfest performance. Carlin was charged with disorderly conduct, fined $150, and put in jail for a few hours. Charges were later dropped and the unforgettable performance piece was given the nickname “The Milwaukee Seven” by Carlin. Historian Matthew Prigge has a more thorough account of this infamous evening in Summerfest history.

3. GG Allin (1991)
After a (literally) shitty 1989 show in which GG Allin threw his feces at an Odd Rock Café crowd, the shocking punk rocker was charged with disorderly conduct and sentenced to 90 days in Milwaukee County Jail. The experience inspired the song “Shove That Warrant Up Your Ass”…or at least it partially did. He got arrested kind of often.

4. Charles Barkley (1991)
Sir Charles Barkley doesn’t mince words when it comes to his feelings about Milwaukee. Perhaps some of the outspoken Hall Of Famer’s opinion of this “dreary-ass city” stems from an experience outside Rosie’s early in his storied career. After a game in 1991, a man (likely inspired by cocktail-conveyed courage) antagonized Barkley on Water Street. The then-Philadelphia 76ers star responded by realigning the dude’s face. After moving the man’s nose “about three-quarters of an inch to the left,” Barkley was arrested at his hotel, charged with a misdemeanor count of battery, and missed the team flight as he sat in jail. During a broadcast this season, the outspoken commentator recalled his night behind bars in Brew City, saying, “I was in jail in Milwaukee one time and I had just as much fun as the people out on the town.”

5. Montel Williams (2011)
In 2011, talk show host and public medicinal marijuana advocate Montel Williams attempted to pass a metal pipe through General Mitchell Airport security. Though he had no drugs with him, Williams—who suffers from multiple sclerosis—was cited for possession of drug paraphernalia. Though he didn’t technically serve any time (or even miss his flight), he was fined $484 and forced to fill out paperwork at the airport, which we imagine could feel like a fate worse than jail to some.

6. Randall Simon (2003)
Everybody remembers when Pittsburgh Pirates infielder Randall Simon (playfully?) clubbed the Italian mascot during the Klement’s Sausage Race one fateful July night. Not as many people recall that the incident—which resulted in a few scrapes and immense scandal—also saw Simon being cited for disorderly conduct, fined $432, and locked up for the night. Hopefully Simon had a good lie lined up for the “What are you in for?” query.

7. Wendy O. Williams (1981)
Singer Wendy O. Williams’ 1981 arrest at The Palms nightclub was already covered by our own Matt Wild as part of our “Infamous Shows” Tracklist last September:

“Long before Miley Cyrus won her way into our hearts by licking a sledgehammer in the video for “Wrecking Ball,” live-wire Plasmatics singer Wendy O. Williams was getting roughed up by police for doing the same thing. During the Plasmatics’ show at Milwaukee’s long-defunct Palms nightclub, Williams got friendly with the heavy-duty wrecking tool, using it to simulate fellatio and masturbation. Unimpressed with Williams’ two-for-one stunt, Milwaukee police officers stopped the show, pinned the singer to the ground, and arrested her on an obscenity charge. Plasmatics manager Rod Swenson was also arrested for obstructing of an officer; after Swenson was found not guilty later that year, all charges against Williams were dropped with a thud.”

8. Yovani Gallardo (2013)
For as bad of a reputation as Wisconsin has for drunk driving, one would think the stigma would stretch to more Milwaukee athletes. Former Brewers ace Yovani Gallardo became the first active player since John Jaha in 1998 to be pinched for driving under the influence in metro Milwaukee. In 2013, Yo threw a few too many back at Leff’s Lucky Town and made the mistake of driving home from the ’Tosa tavern. He was arrested and blew nearly three times the legal limit. After a few hours at the station and a fine he could easily manage from his $7.8M salary that season, Gallardo was a free man.

9. Dustin Diamond (2014)
Yeah, yeah…Dustin “Please don’t call me Screech” Diamond was arrested in Port Washington, which is in a different county than Milwaukee. However, we’re not going to miss an opportunity to mention the Saved By The Bell actor allegedly stabbing some dude at a (surprisingly cozy and affordable) bar on Christmas.

10. Lamont Bentley (1999)
While Diamond’s inclusion on this list stretches the Milwaukee part of the qualification, Lamont Bentley’s involvement pushes the “celebrity” portion. Best/only known for his portrayal of Brandy’s loyal friend Hakeem on UPN series Moesha, the Milwaukee-born semi-celeb’s real-life loyalty found him spending a night in the slammer in 1999. According the police report obtained by The Smoking Gun, the actor was the “star of the benefit” being held at The Empire Room Bar off Silver Spring Dr. on Milwaukee’s north side. The police report says as his friend was being arrested for disorderly conduct in the bar’s parking lot, Bentley yelled “You can’t arrest him. If you’re gonna arrest him, you’re gonna have to arrest me, too.” When officers cuffed Bentley, he allegedly resisted and narrowly missed headbutting an officer. He later pleaded guilty to disorderly conduct and paid a $450 fine. We wouldn’t be shocked if this happened to Q, but to Hakeem?!

About The Author

Tyler Maas
Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.