George Strait and Chris Stapleton in Double Bill at Acrisure; Benedum Hosts Jon Stewart; Pittsburgh Pride 2025 (Sat., 5/31/25)

Two top country artists on the same bill is a real deal, so act now before this special offer expires. George Strait teams up with Chris Stapleton to visit Pittsburgh for a concert at Acrisure Stadium. George Strait is a member of the 100 million club, having sold more than that many records worldwide. He’s a country-music innovator, recognized for steering the music back toward its roots, but in new ways. He’s got street cred—or whatever the country version of street cred is—from his youthful years of living and working on the family ranch in Texas. Strait’s awards and accolades are so numerous that if he doesn’t already have a warehouse manager to look after all the trophies and plaques, he might need one soon. And he’s currently touring in support of his 31st (!) studio album, last year’s Cowboys and Dreamers. 

Chris Stapleton scored a sweep of major awards with his first solo album, 2015’s Traveller: Album of the Year from both the Academy of Country Music and the Country Music Association, the Grammy for Best Country Album, and the Billboard award for Top Country Album. Nor was that a one-shot success, as he’s won many more honors consistently for his work as a performer, composer, and producer. Stapleton has co-written with leading artists such as Kenny Chesney, Luke Bryan, Sheryl Crow, and (wouldn’t you know) George Strait. His fifth and latest studio album is Higher (2023). The concert in Pittsburgh also features special guest Parker McCollum. 5:45 p.m. 100 Art Rooney Ave., North Shore. (R.H., M.V.)

2) Comedian and talk show host Jon Stewart had left Comedy Central’s “The Daily Show in 2015, but when he saw that Trump was running for president again he couldn’t resist returning. His insightful, burning, hilarious wit has many politicians and celebrations feeing his humorous sting. Stewart has garnered numerous accolades, including 23 Primetime Emmy Awards, 2 Grammy Awards, 5 Peabody Awards and the Mark Twain Prize for American Humor. Tonight’s show is sold out. 7:30 p.m. Benedum Center, 7th St. and Penn Ave., Cultural District.

3) The annual Pittsburgh Pride celebration is back for Pittsburgh Pride 2025. The festivities got started last night with the Pride Prom and continues through tomorrow. Today’s events include a free performance by “American Idol” finalist, David Archuleta at 7 p.m. Tomorrow’s shows include a free concert from J Howell at 6:20 p.m. Also performing this weekend are Willam and Lil Mo. There will also be a vendor village, a Bigger Gayer Picnic (sold out), the Downtown Pittsburgh Pride March on Sunday (noon), and plenty of other fun activities. Pittsburgh Pride 2025 will be taking place on the grounds of Allegheny Park West in front of the Pittsburgh Aviary.

4) Dormont’s Live from the Parking Pad music series continues this evening with JGBG, a bluegrass tribute band that performs the music of Jerry Garcia. Also on the bill is Rachel Nawrocki. For more information and tickets visit the Parking Pad website. 7 p.m. 1516 Hillsdale Ave., Dormont.

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