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Showtime Watch Guide: May
/wp-content/images/logos/logo_showtime.png Showtime new originals streaming release calendar for MayShowtime

2021 Watch Guide

Showtime

Black Monday

Black Monday

Season: 3

LAST EPISODE:

Sun, Aug 01, 2021
Our motley crew is ready to embrace the ’90s in all of its outrageous splendor. With the financial world in their cocaine covered rearview mirror, everyone’s favorite do-badders face an existential question – what’s a player to do when their balls have been taken away? The answer... change the game.

Showtime

Desus & Mero

Desus & Mero

Season: 4

LAST EPISODE:

Thu, Jun 23, 2022
The first ever weekly late-night talk show on Showtime features popular TV and podcast personalities Desus and Mero speaking off the cuff and chatting with guests at the intersection of pop culture, sports, music, politics and more.

Showtime

Flatbush Misdemeanors

Flatbush Misdemeanors

Season: 2

LAST EPISODE:

Sun, Aug 21, 2022
Neighborhood best friends and urban millennials Dan and Kevin hilariously climb the ladder to nowhere in Flatbush, Brooklyn. But even inside the losing, they find there are little wins that come from tackling hipsters, mental health issues and the rising tide of gentrification.

Showtime

City on a Hill

City on a Hill

Season: 3

LAST EPISODE:

Sun, Sep 25, 2022
Season three brings us to Boston's high society Beacon Hill. Having left the FBI and thrown his badge into Boston Harbor, Jackie Rohr lands a lavish new gig running security for a wealthy family. Life is good until secrets begin to unravel. When an investigation opens, ADA Decourcy Ward sees an opportunity to finally rip out the machinery perpetuating a broken criminal justice system. Siobhan Quays, representing a construction worker who was severely injured on the Big Dig, encounters the city's corruption firsthand, all while coping with the traumatic events of her past year. As Jenny Rohr can attest, given her history with her father, some experiences will haunt you beyond your breaking point.

Showtime

Ziwe

Ziwe

Season: 2

LAST EPISODE:

Sun, Dec 25, 2022
Never afraid to go there (or anywhere), ZIWE presents the hottest of hot button topics and she’s guaranteed to touch a whole lot of nerves. Everything you’ve always wanted to know about Critical Race Theory, Gay Pride, Woke Capitalism and more but were too uncomfortable to ask. Plus, she’s bringing plenty of musical numbers, interviews, guest stars and hilarious sketches along for the ride.

Showtime

Couples Therapy

Couples Therapy

Season: 3

LAST EPISODE:

Fri, May 26, 2023
Far from reality-show caricatures, this is true documentary filmmaking that brings viewers into the authentic and visceral experience of weekly therapy with four couples. World-class therapist Dr. Orna Guralnik deftly guides the couples through the minefield of honest confrontation with each other and with themselves, revealing the real-life struggles — and extraordinary breakthroughs — typically hidden behind closed doors.

Showtime

The Chi

The Chi

Season: 6

NEXT EPISODE:

Sun, May 12, 2024
This season, life in the Chi reverberates between the highest highs and lowest lows. Big dreams are finally realized but at a cost and everyone will be tested in unimaginable ways as they calculate the risks and rewards of their next big move.
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