Comedy shows dominate stages in St. Louis this October. Seven-time Emmy Award–winner Adam Sandler brings his “You’re My Best Friend” tour to town, plus DC Young Fly and homegrown comedic talents Nikki Glaser and Kathleen Madigan will stop by the Gateway City.
Rock ’n’ roll reigns in autumn with performances from Plain White T’s, We the Kings, Lifehouse and Ludo, this October. T-Pain and Playboi Carti will bring a dose of new-school and old-school hip-hop bangers.
Grove Fest
When: 3 p.m. Oct. 4
Where: Grove Neighborhood, Manchester Avenue
How much: Free
More info: stlgrovefest.com
Right before music festival season in St. Louis concludes, Grove Fest returns to Manchester Avenue for its 20th year. This one-day festival shuts down the Grove neighborhood for an evening of music, food, community and entrepreneurship. This year, New Zealand rock band Unknown Mortal Orchestra headlines. Festivalgoers can also enjoy sets from St. Louis–based hip-hop artists NandoSTL and KV the Writer and rock acts Aragon and Jesus Christ Supercar. Grove Fest is family-friendly until 6 p.m., with adult-only festivities kicking off in the evening. This event is also pet-friendly, so bring your furry friends along for the fun.
DC Young Fly
When: 4 p.m., 7 p.m., 9:30 p.m. and 10 p.m. Oct. 4-5
Where: Helium Comedy Club, 1151 St. Louis Galleria St., Richmond Heights
How much: $57.60-$68.95
More info: st-louis.heliumcomedy.com
Atlanta comedian DC Young Fly has made a solid name for himself in the laughs industry. He was a Variety Magazine 10 Comics to Watch in 2019, starred on Nick Cannon’s hit show “Wild ’n Out” and hosted the game show “Celebrity Squares.” Beyond the small screen, DC Young Fly has landed notable film roles alongside actors like Danny Glover, Emmy Award winner Eddie Murphy and Kimberly Elise.
Alabama
When: 7 p.m. Oct. 4
Where: Enterprise Center, 1401 Clark Ave.
How much: $39-$120
More info: ticketmaster.com
Get ready for a night of country and bluegrass hits when Alabama performs live at the Enterprise Center. The Fort Payne, Alabama–based band began under the name Young Country in the early 1970s. They hit it big after changing their onstage moniker, landing multiple platinum albums and 27 No. 1 country singles. Expect to hear songs like “Dixieland Delight,” “Song of the South” and “I’m in a Hurry (and Don’t Know Why).”
Ziggy Marley and Burning Spear
When: 7:30 p.m. Oct. 8
Where: The Factory, 17105 North Outer 40 Rd., Chesterfield
How much: $63.701-$129.80
More info: ticketmaster.com
The eldest son of Bob and Rita Marley, Ziggy Marley has had a career full of his own musical highlights. The eight-time Grammy Award-winning Reggae artist released his most recent single, “Drive,” in 2024. Since then, Marley also released a children’s book “Pajammin!,” which encourages kids to decrease screen time and dive into real-life fun like sleepovers and pillow fights instead. He’s joined on tour by two-time Grammy Award–winner Burning Spear for an evening of reggae jams, cultural affirmation and performance activism.
Jonas Brothers
When: 7:30 p.m. Oct. 8
Where: Enterprise Center, 1401 Clark Ave.
How much: $52.85-$530.95
More info: ticketmaster.com
The world has watched the pop boy band the Jonas Brothers grow up before its eyes. Twenty years after the group’s inception, brothers Kevin, Joe and Nick are keeping the rhythm going as they bring two decades of music to the Enterprise Center. The two-time Grammy Award nominees began as teen sensations on the Disney Channel in 2005. They’ve seen their share of ups and down, including disbanding for six years to pursue solo projects. Expect to hear songs from the brothers’ 2025 album “Greetings from Your Hometown,” and fan favorites like “Leave Before You Love Me” and “Sucker.”
Kathleen Madigan ‘The Day Drinking Tour’
When: 7 p.m. Oct. 11
Where: Stifel Theatre, 1400 Market St.
How much: $62.20-$71.50
More info: ticketmaster.com
Florissant native Kathleen Madigan is heading home this fall to perform at the Stifel Theatre. The comedian and television star graduated from McCluer North High School before going on to appear on the “Late Show with David Letterman,” “Last Comic Standing,” andother TV shows. Madigan returns to her old stomping grounds for laughs and possibly a few drinks, though by 7 p.m. it won’t be day drinking anymore.
Adam Sandler
When: 7:30 p.m. Oct. 17
Where: Enterprise Center, 1401 Clark Ave.
How much: $158.15-$223.65
More info: ticketmaster.com
Adam Sandler has always been funny. Whether starring in hit films like “Happy Gilmore 2” and “Waterboy,” playing Opera Man or Cajun Man as a cast member on ”Saturday Night Live” or even producing his own music, Sandler has a natural knack for stirring up laughs. America’s favorite funny guy brings a night of chuckles and stand-up bits to St. Louis in October.
Nikki Glaser ‘Alive and Unwell Tour’
When: 7 p.m. Oct. 24-25
Where: Fabulous Fox Theatre, 527 N. Grand Blvd.
How much: $61-$97
More info: fabulousfox.evenue.net
Nikki Glaser has been on an amazing run these last few years. The St. Louis native wowed with her 2025 Golden Globes hosting gig so much that they’re bringing her back again to host in 2026. Glaser’s unafraid of cancel culture, constantly pushing the boundaries and sometimes drifting into a dark humor on topics like aging, romance and end-of-life plans. The comedy star is returning home for two nights to remind her hometown that, amid fame and fortune, she’s still “Alive and Unwell.”
Ludo ‘HalLUDOween’ with Thor Axe, the New Tropics and the Funky Butt Brass Band
When: 8 p.m. Oct. 24
Where: The Pageant, 6161 Delmar Blvd.
How much: $35-$125
More info: ticketmaster.com
St. Louis-based alternative rock band Ludo made waves when its 2008 single “Love Me Dead” became a hit, leaving a lasting impression on teenage millennials. Seventeen years later, Ludo fans have created a tradition of travelling to the Pageant for HalLUDOween to catch the band in concert. Since its heyday, Ludo has continued to roll out singles and collaboration tracks like “Dead Man’s Party” and “Raumschiff” with TheRealSnens. Expect to hear throwback faves and new material from the band with a different opening act each night.
T-Pain ‘Celebrating 20 Years of T-Pain’ with Armani White and EarthGang
When: 8 p.m. Oct. 24
Where: The Factory, 17105 North Outer 40 Rd., Chesterfield
How much: Sold out
More info: ticketmaster.com
Mr. “Buy U a Drank” is headed to the Factory to celebrate 20 years of hit records, award wins and Nappy Boy Entertainment. T-Pain first hit the scene in 2004 as a signee to Akon’s Konvict Musik record label. A string of top-charting records like “I’m ’n Luv (wit a Stripper)” and “Bartender” established the Tallahassee native as a hip-hop force in the early 2000s. He helped popularize the use of Auto-Tune in modern American music. T-Pain merges hip-hop swag with R&B vocals, so expect a mix of tracks from his 20-year career.
Playboi Carti ‘Antagonist 2.0′ Tour with Ken Carson and Destroy Lonely
When: 7 p.m. Oct. 25
Where: Enterprise Center, 1401 Clark Ave.
How much: $52.40-$471.40
More info: ticketmaster.com
Atlanta rapper Playboi Carti rose to mainstream success after the release of his 2017 song “Magnolia.” Nearly a decade later, Playboi Carti is an influential force in the rage rap genre, a 180-degree about-face from his millennial rap star beginnings. After popular featured verses on Metro Boomin and Future’s “Type S**t” and Travis Scott’s hit song “FE!N,” the Georgia rapper has established his own fanbase of raging hip-hop youngsters. He’s joined by fellow sad boy rappers Ken Carson and Destroy Lonely for a night of rap mosh pits and generational hip-hop hits.
Lifehouse Acoustic
When: 9 p.m. Oct. 25
Where: Delmar Hall, 6133 Delmar Blvd.
How much: $25-$42
More info: ticketmaster.com
Lifehouse lead singer and songwriter Jason Wade has been on the road performing acoustic renditions of the band’s most beloved songs. Wade spent 20 years performing alongside his Lifehouse bandmates after they rocked the Billboard charts with tracks like “Hanging by a Moment” and “You and Me.” Now, he’s taking time to dive into side projects, bringing group classics and new solo material to the stage.
JID ‘God Does Like Paradise Tour’ with Young Nudy
When: 8 p.m. Oct. 28
Where: The Pageant, 6161 Delmar Blvd.
How much: $54.50-$79.50
More info: ticketmaster.com
JID is one of the hottest young rappers in the hip-hop game. The Atlanta native signed to rapper J. Cole’s Dreamville Records in 2017, quickly gaining a reputation for his witty bars, memorable metaphors and southern wordplay. He’s released five studio albums, collaborated with acts like EarthGang and St. Louis native Smino and dominated on featured verses like Offset’s “Bodies.” Enjoy an opening set from rapper Young Nudy before JID performs tracks like “Surround Sound” and “Enemy.”
‘Delilah vs. Juliet’ with the Plain White T’s and We the Kings
When: 8 p.m. Oct. 30
Where: Delmar Hall, 6133 Delmar Blvd.
How much: $38.50
More info: ticketmaster.com
Two years after rock band Plain White T’s sang “Hey There Delilah,” We the Kings followed it up to croon “Check Yes, Juliet.” The millennial rock favorites are linking up on stage in St. Louis for an evening of emo love and heartbreak as they perform newer selections and oldies you might’ve heard on the throwback music video channel Fuse TV. Although We the Kings hasn’t released an album since 2018, Plain White T’s dropped its ninth album in 2023. Grab your black eyeliner, bell-bottom cargo pants and white T-shirts for a night of nostalgic millennial rock music.
Honorable Mention
That Mexican OT with Drodi and RNB.Foemob, 7:30 p.m. Oct. 2, the Factory, $51.45-$240.70, ticketmaster.com
Sam Nash aka October London, 7:30 p.m. Oct. 9, City Winery, 3730 Foundry Way Suite 158, $45-$75, citywinery.com/st-louis
St. Louis Nights Experience: The Homecoming with Travis Porter, 7 p.m. Oct. 10, Atomic Pavilion, 4140 Manchester Ave., $30.10-$66.15, ticketweb.com
Al Holliday and the East Side Rhythm Band, 7 p.m. Oct. 11, Miner’s Theatre, 204 W. Main St., Collinsville, Ill., $20-$23.18, eventbrite.com
Tate McRae, 7:30 p.m. Oct. 11, Enterprise Center, $360.65-$473.90, ticketmaster.com
Pines Fest with the Mighty Pines, the High Hawks and Jake’s Leg, 2 p.m. Oct. 18 Atomic by Jamo, $32.25-$107.35, ticketweb.com
Mali Music, 7:30 p.m. Oct. 18, City Winery, $48-$68, citywinery.com/st-louis
Ozark Mountain Daredevils with Wet Willie and Jimmy Hall, 7:30 p.m. Oct. 19, the Factory, $52.50-$185.95, ticketmaster.com
Lord Huron, 8 p.m. Oct. 24, Chaifetz Arena, $49.25-$242.25, ticketmaster.com
Warren Zeiders, 7:30 p.m. Oct. 25, Chaifetz Arena, $38.95-$253.45, ticketmaster.com
Patty Griffin and Rickie Lee Jones, 8 p.m. Oct. 29, the Pageant, $55.45-$113.30, ticketmaster.com
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Jasmine Osby | Post-Dispatch
Music reporter
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