It’s going to be a big summer for old-school hip-hop acts — and several of Selecta’s best Pittsburgh concert picks for July and August 2026 are also free to attend.
Selecta Runs Down the Best Pittsburgh Concerts Coming in July and August 2026
Souls Of Mischief
July 15, City Winery
Anthemic is how one can best describe 93 ’til Infinity, the breakout album from Bay Area denizens Souls Of Mischief. Part of the larger branch of the Hieroglyphics crew — which consists of Souls, Del Tha Funky Homosapien, Casual, Domino as well as Pep-Love — Souls of Mischief are one of several groups that spawned the left-of-center rhyme schemes that broke the mold of how hip-hop from out West was supposed to sound. 33 years later, they still command the stage with the highest of ability.
Smif-N-Wessun
July 17, City Winery
It’s shaping up to be a very hip-hop-centric week at City Winery, with back-to-back shows featuring groups from the halcyon days of the culture. Emerging from the bubbling underground landscape around the same time as the aforementioned Souls of Mischief, the duo Smif-N-Wessun — consisting of Tek and Steel — helped usher in what was playfully dubbed “backpack rap,” street-oriented lyrics recited over a collection of somewhat dichotomic jazz and soul samples. The way the two trade off bars in such a seamless, symbiotic back-and-forth pattern, it’s almost as if they are one fluid performer.
Rose Royce & Scarface
July 25-26, Hill District Arts Festival
A weekend of free music in Pittsburgh’s historic Hill District will feature Rose Royce, best known for her work on the Car Wash soundtrack, setting things off on Saturday … with an opening DJ set from this writer. Then, Sunday brings a musical journey from the ’90s to the present day with DJ sets from Blakk Steel, Wink, & DJ Coles, punctuated by a performance from Houston’s Scarface. Look to Scarface’s stellar Tiny Desk performance from 2023 for evidence of what to expect from his deeply expressive live show. The festival can be found at 510 Heldman Street and the 1800 block of Centre Avenue.
Arrested Development & Cam Chambers
July 26, Hartwood Acres Park Amphitheater
When it rains it pours, as the old adage states. (Although: Let’s hope for sunny skies.) Another free, outdoor hip-hop concert comes to our fair city — on the same day as Scarface’s headlining performance in the Hill District. Hartwood Acres will host the socially conscious, Atlanta-based group Arrested Development, who brought the world the ubiquitous Everyday People (“Let me hear you say woah …”), a tune that to this day will rock any party with its infectious, call-and-response hook. Group lead Speech continues to push to the envelope with his lyrical and spoken-word prowess; local rising star Cam Chambers, who has vocal chops for days, also opens up the show.
Digable Planets
August 4, Mr. Smalls Theater
I didn’t plan it this way (I swear), but here’s yet another show featuring an iconic ’90s hip-hop outfit. Digable Planets burst onto the scene with a huge initial offering, Rebirth of Slick (Cool Like Dat). Taking a page from the A Tribe Called Quest playbook, the group incorporated jazz licks to make up its musical backdrop. (And the most prominent sample on Rebirth of Slick is a horn riff snatched from the 1978 number Stretching, from Pittsburgh’s very own Art Blakey and the Jazz Messengers.) It’s not often that a group sticks together through the trials and tribulations of the industry; it’s a treat that we get to see all three original members in the funky, fresh flesh.
Roger Humphries: A Tribute to Bill Strickland
August 8, City Winery
This evening highlights two names that Pittsburgh jazz aficionados should know well: the former, for his mastery of the drum kit and his features on several Blue Note and Prestige releases; the latter, for his founding of the Manchester Craftsmen’s Guild, which opened up the world of creativity to at-risk youth — and ultimately provided a home for jazz shows that otherwise would’ve skipped over the ’Burgh. At 82, you can still find Roger gigging around town. On this night, Humphries and his ensemble will offer pieces from some of Bill’s favorite artists. It should be a very special night of paying homage to a great man of the arts.
Story by James Scoglietti
Photo From Arrested Development
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