What to do in Philly: May 27 – June 4

Curated by acclaimed podcaster and writer Len Webb, this listing features the best Philly has to offer in terms of entertainment, comedy, music, community, and more every week.

This year, the famous outdoor event runs June 4 and 5.

Hey, Weekly Phillies – I’m back with another week of fun things to do in Philly, but a funny thing happened as I was curating this week’s edition and adding some personal commentary as usual; scrolling thru the dozens of notices, emails and messages previewing the city’s festivities that crossed my desk. City Winery has compiled such an interesting line-up that it was hard choosing just one to highlight, so here’s the whole weekend.

If that doesn’t get you out of the house, there’s always the Roots Picnic 2022, a Pride Month version of a legendary afternoon tea service with drag queens (natch), and a movie in Clark Park.

Friday, May 27



Conya Doss has a resilient style steeped in the spirit of growth, resilience, and grown-woman femininity. Her recent release “Through Rose-Colored Glasses” continues to build on Conya’s prolific legacy of excellence, which extends to her captivating on-stage persona.
An Evening with Conya Doss; Friday, May 27, 6 p.m. (Doors), 8 p.m. (Show); The Loft at City Winery, 990 Filbert Street.


Drummer/Artist Wes Waktins and his band Got My Own Sound bring their Moonshine Music back to Philly, turning up the Winery stage with their a pot liquor of Hip-Hop, Funk, Soul and Jazz.
Wes Watkins & Got My Own Sound; Saturday, May 28, 6 p.m. (Doors), 8 p.m. (Show); The Loft at City Winery, 990 Filbert Street.


Will Downing’s career spans over 34 years and counting; 24 albums and counting; and now includes a weekly radio show which he hosts called “The Wind Down,” appearing in over 20 stations around the world in the USA, UK, Japan, and Spain proves that Downing is one of the most versatile and most loved voices of our time.* And one of my sister Lesie’s favorite singers of all time.
Evenings with Will Downing, Sunday, May 29, and Monday, May 30; 6 p.m. (Doors), 8 p.m. (Show); Main Stage at City Winery, 990 Filbert Street.


A true comedic heavyweight, “MADtv” standout Aries Spears always comes loaded with the best impressions in the game and a unique take on everything from sports to current events. His quick wit, charisma and ferociously aggressive style of comedy have earned him critical acclaim, high accolades, and above all, a busy schedule. But he’s always got love for Philly.
Special Event: Aries Spears; Thursday, May 26, through Sunday, May 29; Helium Comedy Club, 2031 Sansom Street.


This is it — ‘The best Prince film you’ve never seen!’ No, it’s not “Purple Rain 2: Clouds of Red and Blue.” Prince Rogers Nelson and the most comprehensive iteration of The Revolution ever assembled – Sheila E, baby! – perform 13 numbers, most of them from his double album, Sign O’ the Times. This is high-energy stuff in breath-taking 4K free for your lounge chairs, popcorn, and snapping fingers! Hosted by DJ Duiji 13 and Starfire of Vinyl Tap 215.
cinéSPEAK Under the Stars at Clark Park: Prince’s SIGN O’ THE TIMES *35th Anniversary hosted by Starfire and DuiJi 13 of Vinyl Tap 215; Friday, May 27, 7:30 p.m. (Doors), 9 p.m. (Screening); The Bowl at Clark Park, 4300 Chester Avenue.


The star of “The Parkers proved her dramatic chops when she won the Academy Award for Best Supporting Actress for her role in “Precious.” But her talents don’t end there as she brings the same fire to her first love, stand-up comedy. And she’s armed with the Heavy Hittas of Comedy, too. Glenside – you ain’t ready! *I recently reviewed Precious on my podcast and marveled all over again at Mo’Nique’s performance. Underrated is her other starring feature, Phat Girlz. smart comedy in disguise.
Laff Out Loud presents Mo’Nique; Friday May 27, 6 p.m. (Doors), 7 p.m. (Show); Keswick Theatre, 291 North Keswick Avenue, Glenside, PA 19038



A captivating presence both on record and onstage (and film!), Chrystabell’s hypnotically seductive voice and striking visual presentation have won her an ever expanding army of devoted fans, including the equally creative, film director David Lynch. Her ‘Midnight Star’ tour promises a riveting and conceptual narrative around humanity’s harrowing, failing relationship with this planet Earth.
Chrystabell; Saturday, May 28, 7 p.m. (Doors), 7:30 p.m. (Show); Silk City, 435 Spring Garden Street.


The Beatles have The Fab Four (to name one of many). The Grateful Dead’s got Terrapin Flyer. Rock group tribute bands are a dime a dozen. Now, a tribute band to a rapper, a legendary hip-hop mega star gone too soon yet forever remembered? That’s The Frank White Experience, the living, breathing full instrumentation of the greatness of The Notorious B.I.G., plus the very best of 80s-90s hip-hop. I can not express how dope* I think this is. * Feel free to substitute ‘dope’ with an appropriate exclamation of your choice, befitting your generation.
The Frank White Experience: A Live Band Tribute to The Notorious B.I.G.; Saturday, May 28; 7 p.m .(Doors), 8 p.m. (Show); Brooklyn Bowl Philadelphia, 1009 Canal Street. 



Since 2012, The Philadelphia Latino Film Festival (PHLAFF) has become the Greater Philadelphia region’s only festival showcasing the extraordinary and innovative work of emerging and established Latine/x/a/o filmmakers to a wider audience. It has evolved into a space where filmmakers, actors, producers and creatives can meet with other artists, engage with audiences and discuss innovative work. For a full schedule with times and locations, please visit their website.
11th Annual Philadelphia Latino Film Festival; Sunday, May 29 through Sunday, June 5; Various Locations. 



A groundbreaking panel discussion amplifying queer voices to raise the volume on important issues of equality, acceptance, and impact, kicking off Philadelphia Pride weekend inside the event space at W Philadelphia. Moderated by Philadelphia-based writer and Executive Director of Asian Arts Initiative Anne Ishii, the discussion will cover the evolution of queer voices and discuss what the future of allyship in Philadelphia looks like in nightlife, media, and public space. Come early to check out the Bootleg Fantasy Art Show by artist Brad Hoseley, too; that opens at 5 p.m. before the panel discussion.
QUEER ME OUT | Creating Space: The Impact of Queer Trailblazers, Friday, June 3, 7 p.m.; W Philadelphia, 1439 Chestnut Street.



Two days. Living it up with your fellow weekly Phillies in the sun at The Mann and look at all those Grammys on the stage! The Roots with Mary J. Blige. Jazmine Sullivan. Summer Walker. Keyshia Cole. Musiq Soulchild. SWV. Wizkid. DJ Jazzy Jeff. Rakim. Rick Ross. Why are you still reading? Kirk Franklin. Kamasi Washington. Yebba. Benny The Butcher. Robert Glaspar. Bilal. Are you still reading? Tickets gonna be gone; smash that link, ya crazy! Jemele Hill Is Unbothered…because she’s on Podcast Row with tickets! Mickey Guyton. Chief Keef. Suzann Christine. OW, my fingers numb. * Watching a show at The Mann is like a Maxx’s cheesesteak. It taste so damn good, every bite. Scooping up the drop-off from the paper. You’re sad when it’s over; when it’s gone but that flavor….you can live on that for couple of days, yessir.
Roots Picnic 2022; Saturday, June 4, and Sunday, June 5, 1 p.m. (Doors); The Mann at Fairmount Park, 5201 Parkside Avenue. 


Sofitel Philadelphia kicks off Philly Pride Month with the celebrated drag tea expanded to all four weekends of June this year— Saturdays, June 4, 11, 18, and 24, 2022.  Look for a new spin on a time-honored tradition. Sofitel, famous for its classic afternoon tea service, will debut a new Drag Tea featuring Brittany Lynn’s Drag Mafia. Sip tea (or spill it) in the presence of fabulous drag queens as you enjoy delicious offerings from Sofitel’s award-winning culinary team.* Is it wrong that I just want to be in the room when this happens? If only it’s as dishy as The Gilded Age.
Sofitel Philadelphia presents DRAG TEA; Saturdays in June, 2 p.m. to 4 p.m.;  Sofitel Philadelphia at Rittenhouse Square, 120 South 17th Street.

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