What’s on Showtime in May 2020? ‘Billions’ Season 5 Premiere and Classic Rom-Coms Streaming This Month

Millions of Americans are gearing up to spend another month in coronavirus (COVID-19) lockdown. While spending more time indoors might not be your cup of tea — especially as the weather heats up — Showtime is doing its part to keep you entertained with new episodes of its original shows and some compelling additions to its streaming movie lineup. Here’s what to stream on Showtime in May 2020. 

‘Billions’ Season 5 premieres, plus new episodes of ‘Penny Dreadful: City of Angels’ 

Paul Giamatti as Chuck Rhoades and Damian Lewis as Bobby “Axe” Axelrod in Billons | Jeff Neumann/SHOWTIME

Showtime’s hit drama Billions returns with new episodes on Sunday, May 3. But there’s a catch: Production on the show shut down early because of the pandemic, which means fans will only see the first seven episodes; the rest of the season should air later in 2020.

In season 5, the rivalry between Bobby Axelrod (Damian Lewis) and Chuck Rhoades (Paul Giamatti) heats up again. At the same time, there are new threats on the horizon. Corey Stoll (House of Cards) joins the cast as a social impact pioneer who challenges hedge-fund manager Bobby, while Chuck is feuding with a district attorney. Taylor Mason (Asia Clark Dillon) ends up forced to back Axe Capital to protect its employees and assets, while Wendy Rhoades (Maggie Siff) reevaluates her loyalties and makes moves that could put her at odds with both Chuck and Axe. Plus, Julianna Margulies joins the cast as professor and best-selling author Catherine Brant. 

New episodes of Penny Dreadful spinoff Penny Dreadful: City of Angels will also continue to air on Sundays. This new show star Natalie Dormer as a supernatural demon in 1938 Los Angeles, as well as Daniell Zovatto and Nathan Lane as a pair of detectives investigating a grisy murder that ties into the city’s rich and complex history. 

Showtime subscribers can also stream a new comedy special on Friday, May 29: Jesus Trejo: Stay at Home Son. This hour-long special “is packed full of candid humor as Trejo gives us a front-row seat into the amusement within his family dynamic” as the only child of immigrant parents. 

Binge on rom-coms this month on Showtime 

Showtime is also highlighting it’s binge-worthy lineup of rom-coms this month. This May, you can stream classics such as Bridget Jones’s Diary, My Best Friend’s Wedding, She’s All That, Sleepless in Seattle, and While You Were Sleeping.

A number of new movies also make their Showtime debut this month, including Red Joan, Ophelia, Basketball County: In the Water, and Paradise Hills

Here’s the complete list of what’s coming to Showtime in May 2020. 

Available May 1: 

4:44: Last Day On Earth

A.I. Artificial Intelligence

Almost Famous

Armored

Back to the Future

Back to the Future Part II

Back to the Future Part III

Beauty Shop

The Big Chill

Big Fish

Blue Chips

Bull Durham

Carriers

Changing Lanes

Cheech & Chong Still Smokin

Chicago

The China Syndrome

City Slickers

City Slickers 2: The Legend of Curly’s Gold

Cop Land

Dick

Double Impact

Down to Earth

Failure to Launch

The Game of Their Lives

Head of State

Kill Bill: Volume 1

Kill Bill: Volume 2

A Knight’s Tale

Mean Girls

Mousehunt

The Murder of Nicole Brown Simpson

My Best Friend’s Wedding

An Officer and a Gentleman

Orange County

The Other End of the Line

Our Idiot Brother

Peace, Love & Misunderstanding

Rocky

Rocky Balboa

Rounders

Rudy

The Saint

The Samaritan

Seven

She’s All That

Snow Day

Something’s Gotta Give

St. Elmo’s Fire

Staying Alive

Steel Magnolias

Stomp the Yard

Stomp the Yard: Homecoming

Terms of Endearment

Tyler Perry’s Meet the Browns

Under the Tuscan Sun

The Usual Suspects

Varsity Blues

Virtuosity

War

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Available May 2: 

Apollo 18

Red Joan 

Available May 5:

Zero Days

Available May 10:

Speed of Life

Available May 13:

Ophelia 

Available May 15: 

Basketball County: In The Water 

Available May 16: 

Atonement

Paradise Hills

Available May 23:

The Last Movie Star

Available May 29:

Jesus Trejo: Stay At Home Son