Plan Your Week: The Best Pittsburgh Events May 25-31

The week’s best Pittsburgh events from May 25-31 begins with cinema’s biggest icon and winds up with a poignant love story. (Admittedly, a bit of a journey.) Read on for our picks in theater, film, nightlife and more — including dogs at the ballpark!

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The Best Events in Pittsburgh May 25-31

Godzilla Minus One

Monday, May 25, AMC Theaters

The surprise 2023 hit Godzilla Minus One might be the best film about the giant monster. Less a kaiju rampage and more a tale of trauma in postwar Japan, the modestly budgeted film upset offerings from major studios to win an Academy Award for Best Visual Effects. A sequel is due out later this year; in the meantime, see Godzilla Minus One on the big screen, revived by AMC as part of its Asian American Heritage Month series.

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Pirates Pup Night

Tuesday, May 26, PNC Park

If you’re a lover of both dogs and America’s pastime, you are likely well aware of PNC Park’s Tuesday-night Pup Night promotion, wherein a specially purchased ticket admits not only one human but also one dog to a reserved section of seats. (We already have our chihuahua, Peanut, booked for a game later in the season; we’re considering outfits.) But consider this opportunity as a fan: If the Pirates do well, it’s a great night at the ballpark. If the Pirates struggle, you can just look at all the nice dogs. It’s a win-win.

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Toadies

Wednesday, May 27, Roxian Theatre

The alternative-radio mainstays Toadies, best known for the sinister yet irresistible hit Possum Kingdom, are the headliners at this midweek show in McKees Rocks. Don’t arrive late, however, as the full lineup is worth your attention. The band will also be joined by fellow post-grunge outfit Local H and the western-tinged Vandoliers; the latter band is a personal favorite of mine, with a delightful fusion of punk and country.

Walk With Me Screening and Reception

Thursday, May 28, Union Trust Building

The documentary Walk With Me offers a rare personal look at early-onset Alzheimer’s, as accomplished casting director Heidi Levitt steps behind the camera to capture the journey of her husband, Charlie Hess, who was diagnosed with the disease at 57. The film will receive its local premiere on Thursday night in a screening as well as reception benefitting the Clear Thoughts Foundation, a nonprofit that works toward treatments for dementia. The evening is a chance to see a powerful documentary — in an impressive setting, the stately Union Trust Building. (Since it’s a private space, all tickets must be purchased in advance, and include access to the reception.)

The Great Gatsby

Friday, May 29, Benedum Center

The 2025-26 Broadway in Pittsburgh season concludes with a local premiere — and a lush adaptation of a beloved piece of literature. The Great Gatsby, still running today on both Broadway and the West End, features a jazz-influenced score by Grammy winner (and frequent Broadway producer) Jason Howland. The production has become known for its Jazz Age aesthetics and spectacle; in fact, it took home a Tony for its costume design. Try to dress to match — and make a night of it, old sport.

Attack Theatre’s Thirty Ball

Saturday, May 30, Rockwell Park

The Dirty Ball, the annual fundraiser for cutting-edge dance and performance outfit Attack Theatre, has a reputation as one of the city’s most intriguing parties; in their own words, “a bold blend of elegance, energy, and just the right amount of mischief.” You can expect a major milestone edition — the aptly named Thirty Ball, in honor of the organization’s 30th anniversary — to be elevated even higher than the typically impressive standard for the event. Catch surprising performances and more, as the party takes over a floor of Rockwell Park in Point Breeze.

Talley’s Folly

Sunday, May 31, South Park Theatre

It’s an odd-couple love story in real time: Talley’s Folly, which won the 1980 Pulitzer Prize for Drama, takes place in 97 minutes with no scene changes or interruptions. (The title character promises as much as the play begins.) It’s an intriguing and rich challenge for actors and an unusually realistic depiction for audiences — perhaps explaining why companies have gone back to Lanford Wilson’s play for more than four decades. South Park Theatre presents this two-hander at their charming home base through Sunday. (And you can add a picnic lunch!)

Plus, check out our calendar for other events for the week and beyond!

Story by Sean Collier
Photo by Harrison Barden From Pittsburgh Pirates 

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