New Seasons of ‘The Chi,’ and ‘Black Monday,’ Plus Everything Else Streaming on Showtime in May 2021

Showtime has a stacked slate for May 2021. Among the fresh offerings from the premium cable network are new seasons of The Chi and Black Monday, plus the premiere of the new variety series Ziwe. Plus, dozens of new-to-Showtime movies will be available to stream, including Born on the Fourth of July, Django Unchained, and Blue Velvet. 

‘Ziwe’ premieres May 9 

Showtime kicks off the month with the series premiere of Ziwe on Sunday, May 9. The all-new late-night variety show features writer-comedian Ziwe and her provocative brand of humor. The show features interviews, musical numbers, guest stars, and sketches, as well as “unscripted and unpredictable” moments with everyday people. 

Also debuting in May is the new 30-minute comedy Flatbush Misdemeanors, created, written by, and starring Kevin Iso and Dan Perlman. It follows Dan and Kevin, who play characters struggling to thrive in their new surroundings in Flatbush, Brooklyn. It premieres Sunday, May 23.

New seasons of Showtime shows ‘The Chi,’ ‘Black Monday’ premiere May 23 

Kevin sitting at a table in a restaurant in season 4 premiere of The Chi
Alex Hibbert as Kevin in The Chi | Elizabeth Sisson/SHOWTIME

Also coming to Showtime in May 2021 are new seasons of The Chi and Black Monday. The Chi Season 4 examines the wide-ranging effects of policing in the Black community after Jake (Michael Epps) has a fateful run-in with a group of officers. Black Monday Season 3 is moving into the ‘90s as Mo (Don Cheadle) dips into the music business with the launch of KokoMo Co Records. Both premiere Sunday, May 23. 

Couples Therapy and City on a Hill wrap up their seasons on Sunday, May 16. The final episode of Desus & Mero before the show goes on hiatus airs Sunday, May 2. 

New Showtime movies in May 2021 

Dozens of new movies are also streaming on Showtime this May. Here’s the complete list. 

  • About Last Night
  • American Honey
  • Annie Hall
  • Arbitrage
  • Biker Boyz
  • Blue Velvet
  • Bopha!
  • Born on the Fourth of July
  • Brimstone
  • Citizen Ruth
  • Complicit
  • Dance With Me
  • Death at a Funeral
  • Death Wish
  • Debunkers, Inc.
  • Delivery Man
  • Devil in a Blue Dress

‘The Chi’ New Cast Additions Hint At What’s To Come in Season 4

  • Django Unchained
  • Fatal Attraction
  • First Sunday
  • Hart’s War
  • Heartbreakers
  • Hoodlum
  • Hulk
  • Inventing the Abbotts
  • Law Abiding Citizen
  • Limitless
  • Longest Yard, The (2005)
  • Love and Honor
  • Mac and Me
  • Masters of the Universe
  • Mid90s
  • No Way Out
  • On the Road
  • Outlaws
  • Rollerball
  • Rosemary’s Baby
  • Sex, Lies, and Videotape
  • Sh*thouse
  • Silver Linings Playbook
  • Texas Rangers
  • The Adjustment Bureau
  • The Art of War
  • The Blackcoat’s Daughter
  • The Captain
  • The Escort
  • The Exorcist
  • The Holiday
  • The Hurt Locker
  • The Legend of Black Charley
  • The Nest 
  • The Queens of Comedy
  • The Reluctant Fundamentalist
  • The Taking of Pelham 1 2 3
  • The Texas Chain Saw Massacre
  • Two Can Play That Game
  • Welcome to the Punch
  • You Got Served

Available May 8:

  • House at the End of the Street

Available May 18: 

  • The Blackcoat’s Daughter

Available May 21: 

  • Moonlight

Available May 22:

  • Dreamland

Available May 28:

  • Lavell Crawford: The Comedy Vaccine 

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