Home » What’s On: HBO Schedule for May 2023

What’s On: HBO Schedule for May 2023

by Jef Dinsmore
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The next iteration of HBO is about to happen. May 23, 2023, is the launch of Max and the death of HBO Max. Certainly, this post will certainly evolve over the next month and how we view the content branded “HBO Original” will see changes as well. Note, however, that we are indeed staying on brand. We are dedicated to following HBO wherever it goes and whatever form it takes. It is still, of course, a cable & satellite destination, but is now only online on Max and via its designated Amazon Channel. Many shows, for a number of reasons, have fallen away or are about to but many others are soon to arrive or are just beginning their development. HBOWatch will be here to follow what is on as always. Stick with us and enjoy. Here is what’s on for May

NOTE: Any content debuting on May 23 or after will stream on WBD’s new site (with the horrible name) – Max.  

A few quick points:

  • The Long Awaited Harrelson & Theroux Arrive
  • So does another Good International Title
  • And don’t forget THE OTHER TWO
  • Plus, strong Documentaries
  • and the end of the troubled HBO MAX!

HBO Original Series: Let us dive in with a long-awaited limited series debut. From Emmy winners David Mandel (HBO’s VEEP), Alex Gregory, and Peter Huyck (HBO’s VEEP) and starring Woody Harrelson and Justin Theroux, the five-episode limited series WHITE HOUSE PLUMBERS debuts MONDAY, MAY 01 (9:00-10:00 pm ET/PT) on HBO and will be available to stream on HBO Max. It takes the audience behind-the-scenes of the Watergate scandal as Nixon’s political saboteurs, E. Howard Hunt (Woody Harrelson) and G. Gordon Liddy (Justin Theroux), accidentally topple the presidency they were zealously trying to protect… and their families along with it. Chronicling actions on the ground, this satirical drama begins in 1971 when the White House hires Hunt and Liddy, former CIA and FBI, respectively, to investigate the Pentagon Papers leak. After failing upward, the unlikely pair lands on the Committee to Re-Elect the President, plotting several unbelievable covert ops – including bugging the Democratic National Committee offices at the Watergate complex. Proving that history can sometimes be stranger than fiction, this work sheds light on the lesser-known series of events that led to one of America’s greatest political crimes.

Cast credits include Lena Headey (Dorothy Hunt), Judy Greer (Fran Liddy), Domhnall Gleeson (John Dean), Toby Huss (James McCord), Ike Barinholtz (Jeb Magruder), Kathleen Turner (Dita Beard), Kim Coates (Frank Sturgis), Yul Vazquez (Bernard “Macho” Barker), Alexis Valdés (Felipe De Diego), Nelson Ascencio (Virgilio “Villo” Gonzalez), Tony Plana (Eugenio “Muscolito” Martinez), Zoe Levin (Lisa Hunt), Liam James (Saint John Hunt), Kiernan Shipka (Kevan Hunt), Tre Ryder (David Hunt), David Krumholtz (William O. Bittman), F. Murray Abraham (Judge Sirica), Rich Sommer (Egil “Bud” Krogh), and John Carroll Lynch (John Mitchell).

–Episode #1 “The Beverly Hills Burglary”
Debut Date: MONDAY, MAY 01 9:00-10:00 pm

A year before the infamous Watergate break-in, E. Howard Hunt and G. Gordon Liddy are tasked with investigating the Pentagon Papers leak, gathering a team of Cubans – all Bay of Pigs veterans – to infiltrate whistleblower Daniel Ellsberg’s psychiatrist’s office. Meanwhile, Hunt and his wife Dorothy get to know the Liddys.

–Episode #2 “Please Destroy This, Huh?” WhiteHousePlumbers
Debut Date: MONDAY, MAY 08 9:00-10:00 pm

While Hunt and Dorothy entertain Liddy and his wife Fran at their exclusive country club, their kids Lisa and Saint John paint a less-than-perfect portrait of the family. Later, on the outs with Nixon’s Attorney General John Mitchell, Hunt and Liddy get a chance to redeem themselves when a leaked memo from Dita Beard puts Mitchell and the administration in legal jeopardy.

–Episode # 3 “Don’t Drink the Whiskey at the Watergate”
Debut Date: MONDAY MAY 15, 9:00-10:00 pm

Hunt, Liddy, and the Cubans attempt to break into the DNC offices at the Watergate to plant listening devices for the White House.

–Episode # 4
Debut Date: MONDAY, MAY 22, 9:00-10:00 pm

–Episode # 5
Debut Date: MONDAY, MAY 29, 9:00-10:00 pmSuccession-OneLastPic-300x146

The final season of SUCCESSION continues for a few more episodes. We were already thrown for a loop when the big, brash Roy patriarch bowed out. But, then again this is about who was to succeed him as the head of his empire, right? It resumes on SUNDAY, MAY 07 @ 9:00 pm ET/PT 

–Episode # 7 “Tailgate Party”
Debut Date: SUNDAY, MAY 07 (9:00-10:05 pm) 

–Episode # 8 “America Decides”
Debut Date: SUNDAY, MAY 14 (9:00-10:07 pm)  

–Episode # 9
Debut Date: SUNDAY, MAY 21 (9:00-10:00 pm) 

–Episode # 10
Debut Date: SUNDAY, MAY 28 (9:00-10:00 pm)


The half-hour shows from last month have some life to them as well. The final season of BARRY has the last three episodes to air in May. The show starts the month on SUNDAY, MAY 07 @10:00 pm ET/PT.  

Though the descriptions don’t offer us much it’s fun to figure out just what they mean. 

–Season 4, Episode 5: “tricky legacies” 
Debut Date: SUNDAY, MAY 07 (10:05-10:40 pm) 

Things have changed. Written & Directed by Bill Hader 

Yes, they have, and not for the better, unless you believe in a redemption story.   

–Season 4, Episode 6: “the wizard” 
Debut: SUNDAY, MAY 14 (10:07-10:40 pm) 

Lock the door. Written by Duffy Boudreau; Directed by Bill Hader 

Is he coming for Sally? Maybe, he’s after Gene and/or Noho Hank?  

–Season 4, Episode 7: “a nice meal” 
Debut Date: SUNDAY, MAY 21 (10:00-10:30 pm) 

I was talking about office supplies! Written by Liz Sarnoff; Directed by Bill Hader 

What, does he get a new life in witness protection selling staplers? And is that a good idea? He probably knows how to use a stapler as a weapon.

–Season 4, Episode 8: Debut Date: SUNDAY, MAY 28 (10:00-10:30 pm)  

SomebodySomewhere_S2Poster-229x300SOMEBODY SOMEWHERE is just two episodes into its season. That means five more to go starting SUNDAY, MAY 07 10:30-11:00 pm ET/PT. The show starring and executive produced by comedian and singer Bridget Everett offers us a platonic relationship that is really working. Grappling with loss and acceptance, singing is Sam’s saving grace and leads her on a journey to discover herself and a community of outsiders who don’t fit in but don’t give up, showing that finding your people and finding your voice, is possible. Anywhere. Somewhere. Season two reminds us that families are hard, even the fun ones. Sam and Joel (Jeff Hiller) have settled into a comfy routine. But nothing stays the same forever.

–Season 2, Episode 3: “SLS”
Debut Date: SUNDAY, MAY 07 (10:40-11:10 pm)

As Mary Jo’s behavior worsens, Sam and Tricia grapple with the difficult decision of escalating her care. Then, as Tricia pitches her services for Fred and Susan’s wedding, Joel has a crisis of faith, and Sam struggles to get back in touch with her instrument.

–Season 2, Episode 4: “Keys Phone Cash ID”
Debut: SUNDAY, MAY 14 (10:40-10:10 pm)

While on their way to Wichita, Sam and Tricia finally tell Mary Jo why they’re temporarily moving her from the care facility. After accidentally blowing his own cover stalking Brad, Joel opens up about his personal crisis stemming from Fred’s upcoming wedding.

–Season 2, Episode 5:
Debut Date: SUNDAY, MAY 21 (10:30-11:00 pm)

–Season 2, Episode 6:
Debut Date: SUNDAY, MAY 28 (10:30-11:00 pm)

–Season 2, Episode 7:
Debut Date: SUNDAY, MAY 28 (11:00-11:30 pm)

Hey, if you are missing A BLACK LADY SKETCH SHOW then you are missing shit like this –

The final three installments of the season are in May.  

–Season 4, Episode 4: “My Love Language Is Words of Defamation”   
Debut Date: FRIDAY, MAY 05 (11:00-11:30 pm)    

A Black Lady Courtroom hears a new case; a queen’s knights share gossip from around the kingdom; a waitress riles up her customers. 

–Season 4, Episode 5: “Peek-A-Boob, Your T***y’s Out”    
Debut Date: FRIDAY, MAY 12 (11:00-11:30 pm) 

Cousin Curtis mans a hotel front desk; a woman’s hot date with herself gets interrupted; three friends compete for a picture-perfect life. 

–Season 4, Episode 6: Season Finale  
Debut Date: FRIDAY, MAY 19 (11:00-11:30 pm) 

LWTLatestREAL TIME WITH BILL MAHER has wrapped up 1Q of season 21, a huge 35-episode stint. The show continues its task of political and social discourse starting FRIDAY, MAY 05 10:00-11:00 pm ET. His latest sit-down was with Elon Musk. LAST WEEK TONIGHT WITH JOHN OLIVER, the satirical, insightful, and meticulously researched look at current events in the U.S. and around the globe, resumes beginning SUNDAY, MAY 07 (11:00-11:30 pm ET). Lately, the show has scrutinized the necessity of solitary confinement, the HOA game, the continued plight of farmworkers, and the latest on cryptocurrency. Visit the hot tops weekly with Maher & Oliver on HBO.

Original Series Exclusive to HBO Max/Max: If you follow this, you know we are through but that we don’t mention every show imported from another WBD property. That leaves us with just a few titles this month. That will change with the arrival of MAX, but more on that at a later time. Right now, we focus on the following titles.  

First up is SMARTLESS: ON THE ROAD. This gig follows Will Arnett, Jason Bateman, and Sean Hayes during the North American tour of their hit podcast. Directed by Sam Jones (“JASON ISBELL: RUNNING WITH OUR EYES CLOSED), the six-part docuseries provides fly-on-the-wall, intimate access to the three friends and beloved actors as they travel through Boston, Brooklyn, Washington, D.C., Chicago, Madison, Wisconsin, and Los Angeles, giving viewers a sneak peek into the minds, conversations, and bonds behind one of the country’s most popular podcasts. It debuts on the new streamer TUESDAY, MAY 23.

Another title to note is THE OTHER TWO, now presenting Season Three. ChaseDreams (Case Walker) and his siblings, after comparing themselves for years to their much-younger pop star brother and their talk-show host mother (Molly Shannon), who’s now more powerful than she could have ever imagined, Brooke and Cary (Heléne Yorke and Drew Tarver) are finally standing on their own two feet – fully “successful” in their own right! And yet, they somehow find themselves comparing themselves to new people once again?

TheOtherTwo-S3-281x300The ten-episode season, created, written, directed, and executive produced by Emmy-nominated former Saturday Night Live co-head writers Chris Kelly & Sarah Schneider, continues with the debut on THURSDAY, MAY 04. That is followed by two new episodes on May 11 and 18, followed by one episode each Thursday leading up to the season finale on June 15. Entertainment Weekly called the series a “searing showbiz satire with blithe brilliance” and Variety praised it for “setting the new standard for TV comedy right now” with its “sharpness” and “soulfulness.”

Also, LOVE & DEATH is still playing out. The limited series has four more installments to offer. It picks up in May on THURSDAY, MAY 04, and uploads the last one on THURSDAY, MAY 25.  Also find new episodes of ROYAL CRACKERS, FIRED ON MARS and WHO’S TALKING WITH CHRIS WALLACE?.

HBO International Titles: Two strong titles appear here in addition to the continuing series #BRINGBACKALICE, PARA – WE ARE KING, and HEADLESS CHICKENS. Uploading MONDAY, MAY 08 is TWO SIDES OF THE ABYSS (Die zwei Seiten des Abgrunds). It is a 3-part miniseries from Germany. Police officer Luise Berg heads for an inevitable catastrophe after her daughter’s murderer is released early from prison. A psychologically complex game of confusion begins in which the boundaries of guilt and innocence, perpetrators and victims, law and justice are constantly blurred. 


Also arriving with two episodes back-to-back, FRIDAY, MAY 19 to be exact, is the series SPY/MASTER. Created by Adina Sădeanu and Kirsten Peters, the six-part espionage drama series starring Alec Secăreanu SpyMaster-Poster-209x300continues with one new episode debuting weekly leading up to the season finale on June 16. SPY/MASTER is set during the height of the Cold War and covers a week in the life of the fictional character Victor Godeanu, played by Secăreanu (“God’s Own Country,” “Ammonite,” “Happy Valley”), the right-hand man and closest advisor to Romanian dictator Nicolae Ceaușescu. However, Godeanu is also a secret agent for the KGB and must escape Romania and Ceaușescu before his cover is blown. With only one shot at staying alive, he uses a diplomatic trip to Germany as a springboard to the United States. Helped by an undercover Stasi agent and former flame played by Svenja Jung (“Deutschland89”), and an up-and-coming CIA agent played by Parker Sawyers (“Southside with You”), Godeanu must elude the KGB and his own country’s spooks, fully aware that his defection is putting his family back home in mortal danger.

HBO Theatrical Movies: Look for an upcoming post related to the presence of movies going forward for WBD. New theatrical titles to the streamer will be different. Here, however, are some titles that a currentMovies_TheHoleInTheGround-207x300 press release touts as worthy of note. Coming to the streamer (and peppered throughout HBO’s schedule) will be THE HOLE IN THE GROUND, which is an A24 title from 2019. One night, Sarah’s young son disappears into the woods behind their rural home. When he returns, he looks the same, but his behavior grows increasingly disturbing. Sarah begins to believe that the boy who returned may not be her son at all. Also, from 2019, is the Best Picture of that year – PARASITE. Perhaps, that movie is getting played in anticipation of the HBO series based on the Bong Joon-Ho work. Also mentioned are 2015’s RUN ALL NIGHT and 50 SHADES OF GREY (unrated version) and 2013’s THE CONJURING. That last title is also singled out because of its potential series from that universe.

Theatrical Movies Exclusive to HBO Max/Max: Straight from the Tribeca Film Festival and a minor theatrical run is LAND OF GOLD. When truck driver Kiran hears pounding from inside his shipping container and finds Elena, a young Mexican-American girl, his already tumultuous life takes a drastic turn as he seeks to reunite her with her family. It uploads SATURDAY, MAY 15

HBO Films Presentation: Here is something we haven’t seen in a good while, an original HBO Films presentation. HBO Films Presentation: Here is something we haven’t seen in a good while, an original HBO Films presentation. HBO Films’ REALITY debuts MONDAY, MAY 29 at 10 pm ET/PT. The film will air on HBO and will be available to stream on Max. Written and directed by Tina Satter and based on her 2019 play, Is This A Room, the film stars Emmy nominee Sydney Sweeney (HBO’s EUPHORIA, THE WHITE LOTUS) and debuted to rave reviews at the 2023 Berlin International Film Festival. On June 3, 2017, 25-year-old former American intelligence specialist Reality Winner is confronted by FBI agents arriving at her home to question her suspected role in the mishandling of classified information. Based on true events, the film’s dialogue is directly from the transcript of their tense and transfixing conversation. HBO takes the hot topic and we can be sure turns it into a cinematic treat. Great place to boast that I haven’t missed an HBO Films work yet. 

HBO Documentary Films: We begin with 1000% ME: GROWING UP MIXED. Through a series of compelling and insightful conversations, Emmy-winning producer, director, host, and comedian W. Kamau Bell explores the experiences of mixed kids and families in the San Francisco Bay Area. The film was inspired Docs_AngelCity-title-300x154by Kamau and his wife Melissa’s desire to better understand what life is like for their mixed daughters, who are navigating issues of identity in a world that often asks them to pick a side. With humor and heart, the film reveals the joys and complexities of growing up mixed in today’s America. It debuts TUESDAY, MAY 02 (9:00-10:00 pm ET/PT) on HBO and will be available to stream on HBO Max. HBO Original three-part documentary series ANGEL CITY, directed by Arlene Nelson (HBO’s NAKED STATES) and executive produced by Academy Award-winners Natalie Portman, Elizabeth Chai Vasarhelyi, and Jimmy Chin, with Sophie Mas, Anna Barnes, and Christine O’Malley, debuts TUESDAY, MAY 16 (9:00-10:00 pm ET/PT). It is a gripping docuseries that goes behind the scenes and onto the pitch of the groundbreaking Los Angeles-based professional women’s soccer team, Angel City Football Club. Pulling back the curtain on the origin story through the 2022 inaugural season of the female-founded and led team, the series reveals the passion and grit needed to build a franchise from scratch and blaze a bold trail in the world of professional sports.

Shaped by Summer’s own reflections, the memories of close family, friends, and colleagues, and filled with the sounds of Summer’s songs, LOVE TO LOVE YOU, DONNA SUMMER is an in-depth look at the iconic artist as she creates music that takes her from the avant-garde music scene in Germany to the glitter and bright lights of dance clubs in New York, to worldwide acclaim, her voice becoming the defining soundtrack of an era. A deeply personal portrait of Summer on and off the stage, the film features a wealth of photographs and never-before-seen home video footage – often shot by Summer herself – and provides a rich window into the surprising range of her artistry, from songwriting to painting, while exploring the highs and lows of a life lived on the global stage. It debuts SATURDAY, MAY 20 (8:00-10:00 p.m. ET/PT) on HBO.

Docs_BeingMarryTylerMoore-PosterHBO Original documentary film BEING MARY TYLER MOORE, directed by Emmy-winning filmmaker James Adolphus (Soul of a Nation) and produced by Lena Waithe, Debra Martin Chase, and Ben Selkow debuts in May on HBO. The exact date is not known currently, for some unknown reason. But look for it in the latter part of the month and on Max. With unprecedented access to Mary Tyler Moore’s vast archive, this documentary will chronicle the screen icon whose storied career spanned sixty years. Weaving Moore’s personal narrative with the beats of her professional accomplishments, the film highlights her groundbreaking roles and the indelible impact she had on generations of women who came after her. She was one of our cinematic gems.

HBO Original Special: Here is another work we’re eager for but have no specific date locked in for it. Sarah Silverman will return to HBO for her new stand-up comedy special debuting this May. The comedy special, her second for HBO, will feature all-new material, taped in front of a live audience at The Wilbur Theater in Boston, Massachusetts. We know it is a fact though because it is promoted on HBO.com. Silverman’s first HBO special, SARAH SILVERMAN: WE ARE MIRACLES, earned her an Emmy for Outstanding Writing for a Variety Special. Sadly, that’s it. We have no title. Nor do we have a teaser and it might not even show up in May. We will, however, keep track of it and let you know. The special, just like the aforementioned MTM documentary might just be holding out for Max.

HBO Max Kids & Family: Cashing in on DC mostly at the moment. Season One of BATWHEELS continues and a new movie entitled LEGION OF SUPER-HEROES drops. Supergirl is a lead player in this one. Plus, there is always SESAME STREET. But the following title is the big focus and a big Kids premiere for Max. Here comes GREMLINS: SECRETS OF THE MOGWAI. It uploads to Max on TUESDAY, MAY, 23. And if you’re clueless then you have a couple of classic movies to watch and the following clip.  

It takes viewers back to 1920s Shanghai where the Wing family first meets the young Mogwai called Gizmo. Sam Wing (future shop owner Mr. Wing in the 1984 Gremlins film) accepts the dangerous task to take Gizmo home and embarks on a journey through the Chinese countryside. Sam and Gizmo are joined by a teenage street thief named Elle, and together, they encounter—and sometimes battle—colorful monsters and spirits from Chinese folklore. Along their quest, they are pursued by a power-hungry industrialist and his growing army of evil Gremlins. The all-star voice cast includes Ming-Na Wen, James Hong, BD Wong, Matthew Rhys, Izaac Wang, and Gabrielle Neveah Green. The series will also feature notable guest stars including Zach Galligan who starred as the hero “Billy Peltzer” in Amblin’s original films. Additional guest voices include Sandra Oh, Randall Park, George Takei, and Bowen Yang.

HBO Sports: REAL SPORTS WITH BRYANT GUMBEL should have its latest on TUESDAY, MAY 23 (10:00-11:00 pm ET). Hey, and we should know who is featured on HARD KNOCKS this coming year soon.

Other Movies & Shows: From Adult Swim comes UNICORN: WARRIORS ETERNAL. It is the next supernatural animated series from five-time Emmy-winning animator Genndy Tartakovsky. The Adult Swim series produced by Cartoon Network Studios echoes the cinematic artistry of Tartakovsky’s past critically acclaimed works, following a team of heroes who reawaken to fight an ominous force throughout eternity. When the reawakening of our heroes manifests in the bodies of new unsuspecting hosts, they must find a way to protect the world against the prevailing darkness. That Adult Swim import, which arrives FRIDAY, MAY 05, is joined by Season Six of RICK & MORTY because it should be.

We can also give a shout-out to a few more classic movies arriving. Maybe, you’ll like to seek out one or two of them. How about PAPER MOON (1973), MIRRORS (2008), MIRROR, MIRROR, (2012), CALVARY (2014), AMERICAN HONEY (2016), or MIDNIGHT SUN (2018)?

Next Month’s Tease: The May Tease featured a song title so, how about another one? How about “Double Fantasy”?   

Last month – Who does “On the Radio” and “Ordinary People” remind you of? The answer: They should remind you of Donna Summer (as we listed one of her songs) and Mary Tyler Moore (as we listed one of her movies). They both get the HBO Documentary Films treatment in May.  

Final Clip: Light on videos this month so, how about a double dip? 

We squeezed this one out above and it made me chuckle. 

And I like this content because it didn’t. 

Enjoy HBO and HBOWatch!

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