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HBO October 2019 Schedule and Cinemax Highlights


While the September lineup has just kicked off, HBO is already giving an early look at its October schedule. In addition to the anticipated HBO October 2019 schedule, we’ve got some highlights for Cinemax as well.

HBO October 2019 Schedule:

HBO Sports documentary Diego Maradona, debuting Tuesday, October 1 (9:00- 11:05 p.m.) spotlights the life of the legendary footballer, who enthralled onlookers across the globe, inspired a generation of Neapolitans and incited controversy. Drawing on more than 500 hours of never-before-seen footage from the Argentine icon’s personal archives, the documentary charts the trials and triumphs of the legendary footballer.

Created by Jay and Mark Duplass (Animals., Togetherness), the late-night, half-hour anthology series Room 104 continues its third season Friday, October 4 (11:00-11:30 p.m.), telling unique and unexpected tales of the characters who pass through a single room of a typical American chain motel. While the room stays the same, every episode of Room 104 features a different story, with the tone, plot, characters, and even the time period, changing with each installment. Tapping into a variety of genres, from dark comedy to poignant drama to musical romance, the stories and characters featured in season three include: a man searching for a cure to his chronic skin condition; the caretaker of an exotic animal looking to make a sale; estranged siblings reuniting to make an investment; and more. Filled with plenty of twists and surprises, the series offers a new discovery from one episode to the next, telling tales of everyday people striving for connection and meaning inside a single room.

After the murder of his son, a snowplow driver goes on a vengefull quest to kill members of a drug cartel in Cold Pursuit, debuting Saturday, October 5 (8:00-10:00 p.m.). The film stars Liam Neeson, Tom Bateman, Tom Jackson, Emmy Rossum, Domenick Lombardozzi (HBO’s Mrs. Fletcher and Boardwalk Empire), Julia Jones (HBO’s Westworld), John Doman, and Laura Dern (HBO’s Big Little Lies and Sharp Objects).

Comic and actor Gary Gulman comes to HBO for comedy special Gary Gulman: The Great Depresh, debuting Saturday, October 5 (10:00-11:15 p.m.), featuring Gulman speaking on mental health issues in a way that is both entertaining and poignant, along with short documentary interludes that provide insight into Gulman’s mental health journey. In the special, Gulman also offers his hilarious observations on a number of topics, including: his admiration for Millennial attitudes toward bullying, masculinity and sports; the reasons he loves basketball and why he tried to avoid playing football in high school; menacing TV news theme songs; how his mother’s voice is always in his head; and much more. Filmed on June 22 at the Roulette Intermedium in Brooklyn, Gary Gulman: The Great Depresh is directed by Michael Bonfiglio (HBO’s May It Last: A Portrait of the Avett Brothers).

Presenting a satirical look at the week in news, politics and current events, as well as addressing broader issues, the Emmy-winning Last Week Tonight with John Oliver  continues its sixth season Sunday, October 6 (11:00-11:30 p.m.), followed by new episodes subsequent Sundays at the same time, with a hiatus on October 20. Taped in New York a few hours before it debuts on HBO, the show is the only weekly news-oriented comedy series to be presented on Sunday night.

Our Boys Trailer: HBO's Upcoming Limited Drama Series

From Hagai Levi (HBO’s In Treatment), Joseph Cedar and Tawfik Abu Wael, Our Boys, concluding Monday, October 7 (10:00-11:00 p.m.), is a captivating limited drama series that follows Simon, an Israeli terrorism investigator, on his search for answers in the wake of the murder of Palestinian teen Mohammed Abu Khdeir, telling the stories of Jews and Arabs alike who were forever changed by a series of horrific events in the summer of 2014.

HBO Documentary Films presents the stories of two mothers and their children in Torn Apart: Separated at the Border, debuting Wednesday, October 10 (9:00-9:40 p.m.). Directed and produced by Academy Award-winning filmmaker Ellen Goosenberg Kent (Crisis Hotline: Veterans Press 1), the intimate film follows two mothers who were each separated from their children in the United States for months and are desperate to reunite with them. After fleeing violence that claimed the life of her husband and two uncles in Honduras, María was detained and separated from her 10- year-old son Alex for 70 days, while Vilma, who fled from her abusive husband in Guatemala, was placed in ICE detention and saw her 11-year-old daughter Yeisvi put in foster care for eight months. The film tracks both women as they navigate a complicated system that has placed their children thousands of miles away with little access to communicate with them. With the help of pro-bono lawyers and community volunteers, Vilma and María eventually reunite with Yeisvi and Alex – and await uncertain futures as their asylum claims are still pending.

Pico da Neblina, concluding its season Friday, October 11 (10:00-11:00 p.m.), is a ten-episode HBO Latino series set in a fictional modern-day São Paulo where marijuana has been legalized. The story follows 29-year-old Biriba (Luis Navarro), a drug dealer who decides to give up his criminal life and enter the legal drug sales industry. Unfortunately for Biriba, going straight is more difficult than he could have imagined. This brave new world of dealing means he has a whole new set of rules to follow, forcing him to reexamine everything he knew as a lowly dealer. To make matters worse, his new career isn’t sitting well with people from his past who desperately want to put him out of business. The series explores the gray area between what is criminal and what is legal, diving into the social and economic consequences drug trafficking can have on not only a person, but their country as well.

Real Time with Bill Maher continues its 17th season Friday, October 11 (10:00-11:00 p.m. live ET/tape-delayed PT), followed by other new editions subsequent Fridays at the same time. Allowing Maher to offer his unique perspective on contemporary issues, the show includes an opening monologue, roundtable discussions with panelists and interviews with guests.

In this sequel to the 2017 film Happy Death DayHappy Death Day 2U, debuting Saturday, October 12 (8:00-9:40 p.m.), follows a young woman who, after being tansported to another dimension, must try and return home while reliving the same day over and over again, all while a killer threatens everyone’s lives. This black comedy slasher film stars Jessica Rothe, Israel Broussard, Phi Vu, Suraj Sharma, Sarah Yarkin, Ruby Modine and Steve Zissis (HBO’s Togetherness).

The acclaimed drama series Succession concludes its second season Sunday, October 13 (9:00-10:00 p.m.). The series explores themes of power, politics, money, and family, played out within a rich and dysfunctional family whose patriarch, Logan Roy (Brian Cox), is CEO of Waystar Royco, one of the world’s largest media and entertainment conglomerates. Beginning where season one dramatically left off, season two follows the Roys as they struggle to retain control of their empire amidst internal and external threats. While the future looks increasingly uncertain, it is the past that portends to ultimately destroy them, as each of Logan’s four children remains focused on personal agendas that may or may not sync with those of their siblings. As Kendall (Jeremy Strong) deals with fallout from his hostile takeover attempt, this season finds Shiv (Sarah Snook) poised to make her way into the upper-echelons of the company, while Roman (Kieran Culkin) decides to reacquaint himself with the business by starting at the bottom, and Connor (Alan Ruck), who’s long eschewed the Waystar machinations, launches an unlikely bid for president. Blending high drama with sharp humor, season two of the series promises plenty of palace intrigue as this emotionally-challenged family navigates a rapidly changing media landscape and the looming question of who will take over in a post-Logan world.

The Righteous Gemstones, a new comedy from Danny McBride (HBO’s Vice Principals, Eastbound & Down), concludes its first season Sunday, October 13 (10:00-10:30 p.m.). The series centers on the Gemstones, a celebrity televangelist family behind a popular megachurch that is also a major money-making enterprise. McBride stars as Jesse Gemstone, the eldest of three grown Gemstone children, who sees himself as a maverick in the ministry game but, as the series begins, receives a blackmail video that could put his reputation at risk. Getting caught up in the hunt for the culprits are Jesse’s sister Judy (Edi Patterson), who is secretly “living in sin” with her fiancé and dreams of escaping the Gemstone compound, and Jesse’s youngest sibling Kelvin (Adam Devine), a pseudo-hipster who always finds a way to get under his brother’s skin. Meanwhile, the family’s patriarch Eli (John Goodman) finds himself in a point of crisis as he mourns the loss of his wife Aimee-Leigh and questions whether the Gemstones are still serving a higher power as they aggressively expand their empire. Also causing a headache for the Gemstones is Baby Billy (special guest star Walton Goggins), Aimee-Leigh’s younger brother, who agrees to minister at a new Gemstone prayer center that riles a local pastor trying to hang on to his flock. Following the antics of this emotionally stunted family in nine episodes, the series is a hilarious, irreverent look at high-living, holyrollers – whose world of mansions, jets, greed and corruption belies their virtuous, godly mission.

Exploring the glamorous, often cutthroat, world of pro football through a group of past and present players striving to stay in the game, Ballers stars Dwayne Johnson as ex-superstar Spencer Strasmore, who has reinvented himself as a financial manager for today’s players. Created by Stephen Levinson (HBO’s Boardwalk Empire) who also serves as showrunner, the hit comedy series concludes its eight-episode fifth and final season Sunday, October 13 (10:30-11:00 p.m.).

Exploring the past and present of the iconic Statue of Liberty, Liberty: Mother of Exiles, debuting Thursday, October 17 (9:00-10:25 p.m.), follows legendary fashion designer Diane von Furstenberg, “godmother” of the statue, in her quest to discover how sculptor Auguste Bartholdi’s dream became a reality and what the statue means to people around the world. The film spotlights almost 70 subjects whose lives have been touched by it, from street artists and factory workers to the families who lived on Liberty Island until their homes were destroyed by Hurricane Sandy.

The first season of the HBO Latino series La Vida Secreta de las Parejas (The Secret Life of Couples), set in São Paulo, followed the life of sexologist Sofia Prado, who ran a center for alternative couples therapy. Sofia dedicated her life to helping others face difficulty and desire but had emotional turmoil of her own. She had hallucinations she needed to keep secret or risk destroying her career. Sofia was also caught up in the personal life of one of her patients, which entangled her in a major corruption investigation. Part political thriller part sexy psychological drama, the series shows how everyone has something to hide. Even from themselves. Season two debuts Friday, October 18 (10:00-11:00 p.m.) on HBO Latino.

Glass, the final installment in the Unbreakable trilogy, debuts Saturday, October 19 (8:00-10:10 p.m.). Bruce Willis, Samuel L. Jackson, Spencer Treat Clark and Charlayne Woodard reprise their Unbreakable roles, while James McAvoy and Anya Taylor-Joy return as their characters from Split, the second installment in the series. Sarah Paulson, Adam David Thompson and Luke Kirby also star.

The groundbreaking media company Axios returns to HBO for four more season two episodes of its documentary news series Axios on Sunday, October 20 (6:00-6:30 p.m.), exploring the world’s most consequential topics in a smart, fast format that mirrors the company’s “Smart Brevity” promise. Emmy winner Matthew O’Neill and Perri Peltz return to direct and produce, continuing to work with leading Axios journalists to highlight the week ahead in politics, business, technology, media, science and other big topics shaping the future. The first four episodes of the second season of Axios aired this past June.

Set in an alternate history where masked vigilantes are treated as outlaws, Watchmen, debuting Sunday, October 20 (9:00-10:00 p.m. ET/PT) from executive producer Damon Lindelof (Emmy winner for Lost; HBO’s The Leftovers) embraces the nostalgia of the original groundbreaking graphic novel of the same name, while attempting to break new ground of its own. Nicole Kassell directed the pilot from a script written by Lindelof. The cast includes Regina King, Jeremy Irons, Don Johnson, Jean Smart, Tim Blake Nelson, Louis Gossett Jr., Yahya Abdul-Mateen II, Tom Mison, Sara Vickers, Andrew Howard, Jacob Ming-Trent and Dylan Schombing.

Starring Academy-award winner Helen Mirren (The Queen, Gosford Park, The Last Station) and Jason Clarke (First Man, Zero Dark Thirty, Mudbound), Catherine the Great, a four-part limited drama series debuting Monday, October 21 (10:00-11:00 p.m.), is set against the politically tumultuous and sexually charged court of Russian empress Catherine the Great (Mirren) who wielded supreme power throughout Russia for nearly half of the 18th century. The HBO/Sky production follows Catherine towards the end of her reign during her passionate affair with Grigory Potemkin (Clarke). Amid scandal, intrigue and immense conflict, they develop a unique and devoted relationship, overcoming their adversaries and together serving as the architects of modern-day Russia through a series of liberalizing reforms.

In June 2018, women in Saudi Arabia were allowed to drive legally for the first time. Set at The Saudi Driving School in the capital city of Riyadh, which caters exclusively to women, Saudi Women’s Driving School, debuting Thursday, October 24 (9:00-10:00 p.m.), follows Saudi women as they embrace a new way of life and the freedom that comes from being behind the wheel. Through intimate interviews and revealing verité footage, the eye-opening film captures how women’s lives are changing in Saudi Arabia, the hope that they have for greater gender equality and the challenges they face in a Kingdom that appears to be making strides forward but continues to silence and jail female activists. The film was directed by Erica Gornall and produced by Nick London.

A young woman who recently lost her mother befriends a widow, but soon finds their friendship to be increasingly obsessive and toxic in Greta, debuting Saturday, October 26 (8:00-9:40 p.m.). The film stars Isabelle Huppert, Chloë Grace Moretz, Maika Monroe, Colm Feore and Stephen Rea.

The HBO comedy series Silicon Valley returns for its seven-episode, sixth and final season Sunday, October 27 (10:00-10:30 p.m.). A collaboration between Mike Judge and Alec Berg, the Emmy-winning and Golden Globe-nominated series takes a comedic look at the modern-day epicenter of the high-tech gold rush, where the people most qualified to succeed are the least capable of handling success. The series stars Thomas Middleditch as Richard, Zach Woods as Jared, Kumail Nanjiani as Dinesh, Martin Starr as Gilfoyle, Amanda Crew as Monica, Jimmy O. Yang as Jian-Yang, Suzanne Cryer as Laurie Bream, Matt Ross as Gavin Belson and Josh Brener as Big Head.

Starring Kathryn Hahn (Emmy nominee for Transparent; HBO’s forthcoming I Know This Much Is True) in the title role, Mrs. Fletcher, a seven-episode limited series debuting Sunday, October 27 (10:30-11:00 p.m.), is based on the bestselling novel of the same name by Tom Perrotta. The series is a dual coming-of-age story chronicling the personal and sexual journeys of an empty-nest mother and her college freshman son, who both embrace their newfound freedom with mixed results. As the series begins, Eve Fletcher (Hahn), a mid-40s single mom who works as the executive director of a senior center, drops her only child off at college and returns home to a very empty house. Meanwhile, Eve’s son Brendan (Jackson White), a popular (though sometimes clueless) jock, finds college is a little more complicated than he expected and struggles to make connections with his more socially and politically aware fellow students. As mother and son find themselves alone for the first time, this sharp, provocative series navigates themes of parenthood, sexuality, love, and identity in a cultural moment when attitudes about gender and sex are evolving rapidly.

Featuring an ensemble cast led by James Franco and Maggie Gyllenhaal, and executive produced by David Simon, George Pelecanos, Nina K. Noble and Franco, The Deuce, concluding its third and final season Monday, October 28 (9:00-10:00 p.m.), chronicles the dying days of Times Square as the heart of the American sex trade. The season begins on the eve of 1985, with the party of the 1970s winding down. 42nd Street has deteriorated into a hive of uncontrolled violent crime and seedy video stores, making urban renewal seem more unlikely than ever before. But change is on the way. Just as VHS overtakes film as the primary medium for porn production and distribution, the lure of the California sunshine, the city’s aggressive takeover of commercial sex properties and the devastating impact of the AIDS epidemic mark the end of an era. Following the interconnected lives of Times Square’s barkeeps, prostitutes, pimps, police, mobsters, porn actors and producers, this third season brings the series’ arc to a dramatic conclusion.

HBO Sports documentary Any One of Us, debuting Tuesday, October 29 (9:00- 10:30 p.m.), is a revealing documentary produced by Red Bull Films, chronicling pro mountain biker Paul Basagoitia’s remarkable journey to recovery after a devastating injury. The film offers an unprecedented look into the traumatic world of spinal cord injuries (SCI).

Real Sports with Bryant Gumbel goes behind the box scores and statistics to tackle timely subjects in the world of contemporary sports. Featuring a top lineup of contributors, the next monthly edition debuts Tuesday, October 29 (10:30 p.m. – 11:30 p.m.).

The Bronx, USA, debuting Wednesday, October 30 (9:00-10:23 p.m.), follows producer George Shapiro, who returns to his hometown of the Bronx after the death of his closest friend, Howard West. Revisiting the streets, stores and memories of his childhood, Shapiro reflects on the singularity of the borough he grew up in and the close friendships he made there that have stood the test of time. Along with George, the film features notable Bronx-ites like General Colin Powell, Alan Alda, Carl Reiner, Rob Reiner and Chazz Palminteri, who share their experiences and what the Bronx means to them. The 83-minute documentary also introduces the next generation of Bronx-ites – the 2017 graduating class of DeWitt Clinton High School, who come from different backgrounds from Shapiro’s class of 1949, but whose passion, drive and emphasis on the power of friendship connects them with those who came before them nearly seventy years ago. A love letter to a special part of New York City and its distinctive residents, The Bronx, USA is a funny, heartwarming and insightful celebration of what connects us across racial backgrounds, cultures and generations, ultimately emphasizing the hope that exists for the future of America.

Cinemax Highlights:

When a once gentle ape is mutated and becomes a raging giant, a primatologist who once took care of the animal must team up with a geneticist to help save both the ape and the city from its destruction in Rampage, debuting Friday, October 4 (8:00-9:50 p.m.). The film stars Dwayne Johnson (HBO’s Ballers).

Foul-mouthed, wisecracking mutant mercenary Wade Wilson (AKA Deadpool) brings together a team of fellow mutant rogues to protect a young boy with supernatural abilities from a brutal, time-traveling cyborg when the action comedy Deadpool 2 debuts Friday, October 11 (8:00-10:00 p.m.). Ryan Reynolds, Josh Brolin, Morena Baccarin, Julian Dennison, Zazie Beetz, T.J. Miller, Brianna Hildebrand and Jack Kesy star. Directed by David Leitch; written by Rhett Reese, Paul Wernick and Ryan Reynolds.

After entering his team into the Rucker Classic street ball tournament in Harlem, a septuagenarian convinces a basketball legend and his old team to return to the court in Uncle Drew, debuting Friday, October 18 (8:00-9:45 p.m.).

On a secluded weekend getaway, a woman (Gabrielle Union) fights to protect her son and daughter from home invaders when the thriller Breaking In debuts Friday, October 25 (8:00-9:30p.m.).

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Mirko Parlevliet
Mirko Parlevliet has been reporting on the entertainment industry since 1998 and founded to cover movie, TV, video game, music, and theme park news.


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