By Nina Cherry
1–3
Brookside Art Annual

Brookside Art Annual celebrates 40 years as a premier showcase. Each May, the art festival attracts over 100 artists (out of a pool of approximately 1,000 applicants) from around the country. From oil paintings to jewelry to ceramics explore a robust display of striking artwork in the charming, historic neighborhood. May 1–3. Times vary. 63rd Street and Brookside Boulevard.
1 & 2
Cinco de Mayo Fiesta

For 100 years, Guadalupe Centers’ Cinco de Mayo Fiesta has packed Westside streets with a vibrant celebration of Mexican culture. To commemorate the organization’s centennial Fiesta, enjoy live music from local bands, children’s activities, plenty of traditional cuisine and more. May 1–2. Times vary. Westside.
8–17
The Great Gatsby

In the Roaring Twenties, flappers defied modest societal norms of womanhood by sporting shorter dresses and hairstyles and embracing nightlife—which included partaking in once-scandalous dances like the Charleston. The Kansas City Ballet pays tribute to this formative era in music and dance with a reimagining of F. Scott Fitzgerald’s The Great Gatsby. Bringing the glitz, glamour and grandeur of the Jazz Age to the Kauffman Center, the production is choreographed by renowned director Septime Webre and features extravagant set design and costumes by Academy Award-winning designer Tim Yip. May 8–17. Times vary. Muriel Kauffman Theatre.
10
Crossroads Flea
If you’re on the hunt for Mother’s Day plans, look no further. Hosted by Mildred’s, this market—inspired by Brooklyn Flea—pops up each second Sunday of the month on 19th Street between Wyandotte and Baltimore streets. Treat Mom to one of KC’s best breakfast sandwiches (and coffee and cocktails) before shopping a wide range of local produce and flowers, artisan-made goods, vintage gems and more. May 10. 9 am. Mildred’s (Crossroads location).
13
Charlie Puth
If you tuned into the Super Bowl this past February, you likely recognize singer-songwriter Charlie Puth from his soulful rendition of “The Star-Spangled Banner.” Although Puth initially rose to popularity posting covers on YouTube, his big break ultimately came from a feature on Wiz Khalifa’s 2015 hit single “See You Again.” Now, Puth comes to Starlight Theatre in support of his latest album, Whatever’s Clever!, for a night of music under the stars. May 13. 7:30 pm. Starlight Theatre.
19
Monarchs Home Opener

KC’s minor league baseball team opens the season with a matchup against the Chicago Dogs. This year’s roster features the return of power hitter and outfielder Isiah Gilliam, along with newly signed players like local standout Marcus Smith, an alum of Pembroke Hill School. To commemorate the home opener, stick around for the post-game fireworks display. May 19. 6:35 pm. Legends Field.
21
Hot Country Nights: Eli Young Band

Hot Country Nights are back, bringing live music to the Power & Light District every Thursday through August. Hailing from Southeast Texas, Eli Young Band kicks off the summertime series with its gritty and down-to-earth Southern rock stylings. Sing along to fan favorites like “Even If It Breaks Your Heart” and “Crazy Girl.” May 21. 7 pm. Kansas City Live!
21 & 22
Ben Rector with the Kansas City Symphony
Folk singer-songwriter Ben Rector’s latest endeavor, Symphonies Across America, is inspired by the past 15 years he’s spent on the road. Performing his catalogue alongside orchestras nationwide, Rector is joined by friend and fellow singer-songwriter Jon McLaughlin. The tour brings the duo’s songs—like McLaughlin’s “Beautiful Disaster” and Rector’s “Make Something Beautiful”—to new heights with lush symphonic arrangements. May 21 & 22. 8 pm. Helzberg Hall.
24
Celebration at the Station
Held each Sunday before Memorial Day, this KC tradition returns to honor fallen soldiers. Tens of thousands of audience members will gather on the lawn of Union Station and the National WWI Museum and Memorial for food trucks and patriotic festivities. The Kansas City Symphony reliably ends its program with a performance of Tchaikovsky’s climactic 1812 Overture (and deploys real canon blasts), immediately followed by a dazzling fireworks display.For those who’d prefer to avoid the crowds, Kansas City PBS broadcasts the festivities from home. May 24. 5 pm. Union Station & National WWI Museum and Memorial.
24
Tech N9ne & E-40

KC’s own Tech N9ne teams up with longtime collaborator and fellow platinum-selling rapper E-40 on the Strange Wid’ It Tour, with the Midland Theatre performance closing out the run. Beyond Tech N9ne’s own music, the rapper has spent more than two decades building record label Strange Music into a hip-hop empire right out of his hometown. Special guest (and Strange Music artist) King Iso joins the line-up. May 24. 8 pm. The Midland Theatre.
28
Carín León
Carín León brings the sounds of Mexico’s Sonoran desert to Kansas City. Weaving regional styles like ranchera and norteño with rock and roll and country, the nine-time Latin Grammy Award winner is best known for songs like “Según Quién” and “Primera Cita.” Leon’s North American tour precedes a September residency at Las Vegas’ Sphere, where the musician will make history as the first Latin artist to headline the mega-venue. May 28. 8 pm. T-Mobile Center.
29 & 30
Big Slick

KC’s favorite fundraiser, Big Slick, returns. For 17 years, this benefit for Children’s Mercy Hospital has brought homegrown celebrities (and their friends) back to their hometown. This year, hosts include Paul Rudd, Saturday Night Live alums Heidi Gardner and Jason Sudeikis, Modern Family’s Eric Stonestreet and more. The celebrity weekend kicks off with a VIP party at The K, where attendees have an opportunity to mingle with the stars, and culminates in a Saturday-night performance at T-Mobile Center. May 29 & 30. Times and locations vary.
29–31
Ed Bassmaster
It’s been 20 years since Ed Bassmaster launched his YouTube channel, building a following for public pranks and quirky character sketches. After a long string of viral videos, he’s sharpened his stand-up chops, delivering observational humor and energetic crowdwork. May 29–31. Times vary. The Comedy Club of Kansas City.
29–31
Festa Italiana
KC’s annual celebration of Italian-American culture returns to Zona Rosa. Across the three days of festivities, enjoy an Italian motorsports show, bocce ball, cooking demonstrations, live performances and more. The music lineup is headlined by KC’s own Kate Cosentino, a former contestant on The Voice now based in Nashville. And of course, food is an integral part of the festivities. Vendors will be serving up everything from arancini to lasagna to tiramisu. May 29–31. Times vary. Zona Rosa.
30
Kansas City Folk Festival
Kansas City Folk Festival returns to Washington Square Park for a full day of free music. This year’s headliner is nine-piece soul powerhouse The Freedom Affair, along with performances from R&B singer Adeta Marie, Flutienastiness and The Soul Patrol, clawhammer banjo player Kaïa Kater and more. Plus, attendees can browse the craft market and grab a bite from food trucks. May 30. 11 am. Washington Square Park.