The 40 Best Movies on Showtime (2019)

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The 40 Best Movies on Showtime (2019)

Showtime offers more than 500 movies streaming on demand. We’ve gone through the catalog and selected our favorites to recommend. Many of these aren’t available on any of the premium cable channel’s streaming competitors. And Showtime is no longer just available to those with a cable package. You can add a subscription to your Amazon, Hulu or PlayStation accounts or access it via Apple, Android or Roku devices.

For extensive guides to the best movies on other platforms like Netflix, HBO, Amazon Prime, On Demand, YouTube, Shudder and The Best Movies in Theaters, visit all our Paste Movie Guides.

Here are the 40 best movies available on Showtime right now.

gotta-give.jpg 40. Something’s Gotta Give
Year: 2003
Director: Nancy Meyers
When you’ve got two giants of cinema exploring love later in life, you can expect great chemistry. That’s what happens with Jack Nicholson and Diane Keaton when the former breaks his streak of dating women in their twenties and falls for the mother of one of his girlfriends (Amanda Peet). With a soundtrack that spans genres and generations (Badly Drawn Boy, Jimmy Cliff, Paul Simon and Django Reinhardt, to name just a few), it’s a worthwhile take on the opposites-attract rom-com. —Josh Jackson

we-own-the-night.jpg 39. We Own the Night
Year: 2007
Director: James Gray
We Own the Night, a thoughtful crime thriller set in 1988 New York, was produced in part by its stars Joaquin Phoenix and Mark Wahlberg, who play conflicted brothers. Wahlberg is the hard-nosed, New York City cop Joseph Grusinski who tries to clean up the city’s drug trade while his brother Bobby Green (Phoenix) manages the hottest nightclub in Brooklyn, an establishment where drugs are a big part of the attraction. A clash becomes inevitable, even more so because their father (Robert Duvall) is the deputy chief of police. Wahlberg’s role is incredibly reminiscent of his performance in Martin Scorsese’s Oscar-winning The Departed, though not nearly as powerful. And Duvall could have called it in and done just as well. Phoenix, however, gives a strong showing as a man unwillingly pulled through a life-threatening transition, greatly improving a fair-to-middling script. Bobby so disdains his family’s idealism that he even changes his last name, a move that unwittingly reveals no police ties to his drug dealer friends. But when his brother is hospitalized by an assassin’s bullet, Bobby agrees to infiltrate the drug ring. There are no dirty cops in We Own the Night. Rather, we see good guys trying to do the right thing. Instead of surprising us with abrupt character changes, director James Gray (Little Odessa) takes us through Bobby’s personal torment in self-discovery as he realizes how strong his blood ties really are. —Tim Basham

high-plains-drifter-movie-poster.jpg 38. High Plains Drifter
Year: 1973
Director: Clint Eastwood 
A ghostly figure on horseback emerges from a distant, hazy heat mirage recessed in the depths of a desert plain. High-pitched banshee wails squeal like souls of the damned crying out from the land of the dead as the drifter rides into the seaside mining town of Lago. Bystanders gaze at the rider with fear, distrust or possibly a startled look of recognition. A stranger has arrived, and all the dark secrets of the town will soon meet the harsh light of day. Clint Eastwood’s second film at the helm as director, High Plains Drifter finds him coming to terms with his Spaghetti past in this direct homage to the films of Sergio Leone. In the town of Lago, there are no innocents. This message is brought home repeatedly with stark close-ups emphasizing features distorted with anger and rage, rendered grotesque with the almost unbearable weight of their sins. Even Eastwood’s drifter is no heroic icon, almost immediately losing the sympathies of the audience by committing a casual rape of an uppity townswoman who ultimately turns out to be just as complicit as everyone else. Despite its cynical depiction of humanity and its dark subject matter, this brooding, yet never gloomy Western gothic keeps its tight hold on you, depicting a town slowly unraveling, turning against itself as its dirty secrets are exposed by a possibly supernatural entity. —Joe Pettit Jr.

band-aid.jpg 37. Band Aid
Year: 2017
Director: Zoe Lister-Jones
At a glance, Band Aid sounds way too adorable to be good: splintering married couple turns fighting words into alt-pop gems and in doing so, resuscitates the marriage. (My internal twee alert sounded the alarm when I first read that mawkish title…) Indeed, Band Aid is terribly charming, but it manages to finds a way to be true, too—a tribute to writer-producer-director-star Zoe Lister-Jones, who deftly steers the film into a caustically optimistic tone that befits the marriage of these flawed and heartbroken people … a most imperfect union that discovers, if not a raison d’être, a way to stay together anyway.
—Chris White

about-a-boy.jpg 36. About a Boy
Year: 2002
Directors: Chris Weitz, Paul Weitz
No stranger to romantic comedies, Hugh Grant delivered perhaps his best performance ever in About a Boy, a different kind of rom-com. Through his relationship with a young teenager, Grant subtly transforms from notorious womanizer into, well, a man capable of loving the beautiful Rachel Weisz. Grant’s relationship with the boy is tender and thoughtful, much like the film itself. —Jeremy Medina

operation-odessa.jpg 35. Operation Odessa
Year: 2018
Director: Tiller Russell
Way back—like, way, way, way back, when the ’80s were becoming the ’90s and the bad guys were Colombian and in some cases, for whatever reason, still also Russian, and you had to be the worst DEA agent ever if you couldn’t make a collar in Miami—there was an émigré Russian Jew who called himself “Tarzan.” Tarzan started American life in Brooklyn, where he found bountiful work as an arson-oriented enforcer for the Gambino family. He then became a super class-act strip-club owner in his spiritual home: Miami, Fla. There, he met a grafter, or dealer, or I’m not sure what you call marina owner Juan Almeida. Having been introduced at Tarzan’s ultra-classy establishment, Porky’s, and by Vanilla Ice, no less, the two became entangled in a little funny business with the government. Showtime would like to take you back—way, way back—to when they Tore Down That Wall and the Soviet Union collapsed. Their documentary Operation Odessa tracks Tarzan, Almeida, and a Cuban “businessman” (spy) named Tony Yestor as they maybe possibly attempt to buy a Russian military submarine and sell it to the Cali cartel for $35 million. I know, it sounds like something straight out of Hollywood. The kind of improbable heist caper where you walk out shaking your head and saying, “Who green-lit that?” Operation Odessa is not filmed in the gritty Cops style that was used in The Trade and it also covers an incident that happened 20 years ago and, other than the fact that Yestor remains an international fugitive, it’s in the past. Maybe that accounts for the more lighthearted style, but whatever the case, director Tiller Russell made good choices here. Operation Odessa observes its subjects from a two-decade remove and uses that stance to play up how flat-out crazy the story actually is. It handles its subject matter with a little bit of irony, pacing that plays up the essential absurdity of the situation, and I applaud it for that. Because it is, in fact, a crazy story. —Amy Glynn

major_league_poster.jpeg 34. Major League
Year: 1989
Director: David S. Ward
Many can laugh at this crazy cast of oddballs, but only a select few can look back and laugh. Because for those in Cleveland and northeastern Ohio, it’s all too real. Not until the second film’s release did the Cleveland Indians finally break out of their 30-year slump. Some will say it was the new stadium. Others, the even more superstitious ones (most baseball fans), may point to the dominance and swagger of Rick “Wild Thing” Vaughn, as portrayed by Charlie Sheen. (Fun fact: Sheen was actually a star pitcher in high school.) Whatever the case, the really bad times are in the past, and let’s hope, for the sake of another one of these movies popping up, they stay there. —Joe Shearer

adventureland.jpg 33. Adventureland
Year: 2009
Director: Greg Mottola
As far as films set in Pennsylvania are concerned, they can’t all be steel mill layoffs and dark political plots: Adventureland is a pitch-perfect coming-of-age story. In the summer of 1987, twenty-somethings James (Jesse Eisenberg), Em (Kristen Stewart) and Joel (Martin Starr, who steals the movie) find each other in the purgatory of the Adventureland Amusement Park (actually Pittsburgh’s historic Kennywood), passing their days operating rides and un-winnable games when they’d rather be anywhere else. Writer-director Mottola’s success lies in his resistance to romanticizing his characters—Eisenberg’s James, in particular, is just as annoying and self-absorbed as a real 22-year-old Oberlin grad, and gets called on it. Likewise, the Pittsburgh of Adventureland is real, an insider’s city, not a city of landmarks. The film explores the day-to-day Pittsburgh of neighborhoods, of patchy, unruly yards, of dive bars, of wood-paneled basements in old brick houses teetering on strenuous hills. To these characters, it’s also a dead-end town from which escape is the best option, lest they wind up like Ryan Reynolds’ maintenance man Connell, committing adultery in his mother’s basement and bragging endlessly about meeting Lou Reed. “Your life must be utter shit, or you wouldn’t be here,” Joel observes to James at the beginning of the film. But Adventureland’s fondness for its city and its flawed characters shines through such self-deprecation. —Maura McAndrew

the-professional.jpg 32. The Professional
Year: 1994
Director: Luc Besson 
I’m not sure when I’ve seen an action film that’s so touching. It could have been incredibly precious and cloying: cute little girl meets strong-silent type neighbor who turns out to be an assassin. But Luc Besson puts just the right amount of edge into his film (how scary is Gary Oldman?). He coaxes a beautiful performance out of Jean Reno—mournful, weary, resigned, tender. And a young Natalie Portman showed very early on why she was destined for greatness. I challenge you to watch the final scene without getting chills. —Michael Dunaway

running-man.jpg 31. The Running Man
Year: 1987
Director: Paul Michael Glaser
While The Running Man lacks the sophistication and dynamic pacing of a certain other Schwarzenegger-starring/dystopian sci-fi/satire film, its entertainment value is nothing to sneer at. Adapted loosely from a Stephen King novel of the same name, The Running Man depicts a future where everyone dresses like they’re at an ’80s-themed Halloween party and citizens regularly tune into a show where convicted criminals must fight to survive against both their fellow contestants and professional killers. Insert Hunger Games reference here. Between the absurd production design and Paula Abdul-choreographed dance sequences, any attempted satire is all but buried in a thick layer of silly. Still, in terms of sheer fun value, this film is quite the gem.—Mark Rozeman

clerks netflix.jpg 30. Clerks
Year: 1994
Director: Kevin Smith 
Does Clerks hold up? That’s a tough question. It’s the exact same movie it was in 1994, obviously, as unapologetically raunchy and jaded as ever. It’s at once barely competent as filmmaking and yet probably the most artistically cohesive and competent work Kevin Smith has ever made. Clerks was never really a great movie, per se, but made a deep impression for two reasons. First off, the rags-to-riches story behind its creation was basically the ultimate summation of the entire 1990s fascination with indie films. Here’s a guy who made an ugly, lo-fi, black-and-white comedy without professional actors for less than a year’s worth of college, and because it had a voice and verisimilitude that hadn’t really hit the big screen yet, he got distribution through the biggest indie film company of the day and the movie wound up making millions. Secondly, if you were a teenager or twentysomething at the time, Clerks was legitimately hilarious. These characters spoke like your friends, or at least like amplified versions of them. It’s far from a great movie, and most of the acting is as terrible as you probably remember, but it still has that middle-class wastrel charm that made it stand out 24 years ago, and some of the jokes still land, even if your taste in comedy has changed greatly since you first saw it. —Garrett Martin

bloody-sunday-210.jpg 29. Bloody Sunday
Year: 2002
Director: Paul Greengrass
Before directing the Bourne movies, United 93 or Captain Phillips, Paul Greengrass won the Golden Bear at the 2002 Berlin International Film Festival and the audience award at Sundance for Bloody Sunday, a movie about the Bogside Massacre in Derry, Northern Ireland. The infamous day in 1972 saw a protest march against internment turn violent when British soldiers shot more than two dozen unnarmed civilians and 13 people died. Based on Don Mullan’s book Eyewitness Bloody Sunday, Greengrass’ script follows one of the march’s organizers, Ivan Cooper (James Nesbitt). Hand-held cameras and the lack of soundtrack give the film an all-too-real feel as the tragedy unfolds. It’s a powerful piece of cinema capturing a terrible day in history. —Josh Jackson

CoverUpintheAir.jpg 28. Up in the Air
Year: 2009
Director: Jason Reitman 
Ryan Bingham (George Clooney) lives his life traveling, and he loves it, even though his job is to fire workers for employers who can’t break the news themselves. The gig’s a downer, but at least he gets to fly. His remote boss is played by the great Jason Bateman, Vera Farmiga plays a fellow traveler, and when these actors pair off they’re fantastic. The film is primarily a portrayal of Bingham’s isolation and the depressing circumstances of his job, and in doing so provides a spot-on illustration of the the life of the jaded business traveller who knows his way around an airport better than his own home. —Ryan Bort

the-reader.jpg 27. The Reader
Year: 2009
Director: Stephen Daldry
Stephen Daldry’s adaptation of Bernhard Schlink’s The Reader is a somber, desolate and profound film that does not shy away from the story’s thematic complexities. David Kross superbly plays Michael Berg, a teenager in post-World War II Germany who embarks on an affair with a stern, serious older woman named Hanna Schmitz (Kate Winslet). A relationship that begins through an act of kindness quickly becomes sexual, tense and volatile. She becomes entranced by the stories Michael reads to her, the grand tales of Homer, Chekhov, Mark Twain and D.H. Lawrence. One of The Reader’s virtues is its great respect for literature, for those fleeting moments in Hanna’s day where she can revel in a world that is not her own. Winslet is astonishing as Hanna, an introverted woman whose past has been locked away so deep inside of her it has robbed her of a future. When the truth about her past is revealed in the film’s second half, the shame of her secret tightens its grip on her throat. Professor Rohl (a terrific Bruno Ganz) tells Michael to learn from the mistakes he’s made so he can avoid them in his own life. But learning signifies understanding, and understanding is the phantom each character in The Reader desperately chases—that elusive resolution not attainable when horrors this tragic happen at your own doorstep, when the people responsible are staring you in the face. —Jeremy Medina

donnie-darko.jpg 26. Donnie Darko
Year: 2001
Director: Richard Kelly
Apparently, at some point in its burgeoning cult ascendency, director Richard Kelly admitted that even he didn’t totally get what’s going on in Donnie Darko—going so far as to release a “Director’s Cut” in 2005 that supposedly cleared up some of the film’s more unwieldy stuff. Yet another example of a small budget wringed of its every dime, Kelly’s debut crams love, weird science, jet engines, superhero mythology, wormholes, armchair philosophy, giant bunny rabbits and Patrick Swayze (as a child molester, no less) into a film that should be celebrated for its audacity more than its coherency. It also helps that Jake Gyllenhaal leads a stellar cast, all totally game. In Donnie Darko, the only thing that’s clear is Kelly’s attitude: that at its core cinema is the art of manifesting the unbelievable, of doing what one wants to do when one wants to do it. —Christian Becker

tootsie.jpg 25. Tootsie
Year: 1982
Director: Sydney Pollack
Can you imagine how audiences and critics might react to Tootsie if it came out in theaters today? Sydney Pollack’s film plays with gender roles and layers its portrait of an actor going full-drag with gay panic for giggles. You can just picture this film getting lambasted in 2015 for making a joke out of homophobia and for having the gall to ask viewers to sympathize with the plight of an actor who has to dress as a woman to find work. But the reason Pollack’s 1982 classic endures is because of its compassionate heart. This is a kind, empathetic movie that puts its hero, Dustin Hoffman’s cranky perfectionist thesp Michael Dorsey, in the shoes of his female peers to teach him (and us) a lesson, not to make snide jokes at the expense of the opposite sex. The humor is never mean-spirited; the message is rarely pompous, though when it is, that’s meant to be part of the point. Tootsie’s sharp comedy makes it a great piece of entertainment, but it’s the film’s sincere sensitivity that makes it timeless.—Andy Crump

killer-inside-me.jpg 24. The Killer Inside Me
Year: 2013
Director: Michael Winterbottom
British director Michael Winterbottom has yet to really break out in the American box office, but that’s probably because he couldn’t care less. His films run the gamut from purposefully difficult (A Cock and Bull Story) to the unhinged (24 Hour Party People) to the pitch dark (The Road to Guantanamo). Set in West Texas, this thriller from the director of is based on Jim Thompson’s 1952 noir-western pulp novel, previously adapted into film in 1976. It debuted at Sundance before getting picked up by IFC. Casey Affleck turned in one of the most chilling performances in recent memory as Lou Ford, who comes across as your average sheriff’s deputy. His turn as a ruthless, sociopathic murderer is hard to watch, but impossible not to admire. —Michael Dunaway

tombstone.jpg 23. Tombstone
Year: 1993
Director: George P. Costmatos
Tombstone immediately gains the “Sam Elliot bump,” whereby a film with Sam Elliot appearing in it just got that much better, but it’s really Val Kilmer that makes Tombstone perhaps the best (and most purely entertaining) Western of the ’90s outside perhaps Unforgiven. As the sickly gunfighter Doc Holliday, he got the best role of his entire career, radiating both supreme confidence and extreme vulnerability in every scene, stealing the show from Kurt Russell. His final confrontation with Johnny Ringo is a great character study of two alpha males; a true “This town ain’t big enough for the both of us” situation. One of the best popcorn entertainment Westerns of all time. —Jim Vorel

prince-sign.jpg 22. Prince: Sign O’ the Times
Year: 1987
Director: Prince
Prince’s 1987 concert documentary is one hour and 24 minutes of a generation’s greatest musical performer at the peak of his career (sorry, Boss). With his touring band that included Sheila E. on drums, Miko Weaver on guitar, Levi Seacer Jr. on bass, Eric Leeds on sax, Boni Boyer and Dr. Fink on keyboards, and Cat Glover dancing, the film pulls mostly from his 1987 double-album Sign O’ the Times, with hits like the title track, a piano interlude of “Little Red Corvette” and “U Got the Look.” It was filmed at two European shows, but much of the music was re-recorded later at Paisley Park. Still, it has an urgency that only Prince can deliver, in multiple outfits, of course. Released theatrically in the States, the film received more love after it left theaters. Now it’s one of the best ways to see what the big deal is about a Prince concert. —Josh Jackson

ghost-world.jpg 21. Ghost World
Year: 2001
Director: Terry Zwigoff
Terry Zwigoff’s appropriately somber, stylish, brutally honest yet surprisingly tender Ghost World, adapted by Daniel Clowes and Zwigoff from Clowes’ comic, intimately captures the post-high school struggles of Enid (Thora Birch in perhaps the best performance of her career), a too-cool-for-school type who puts on a seemingly impenetrable exterior of ironic detachment as an attempt to hide her ever-growing insecurities regarding the adult life that’s rearing its ugly head more and more each passing day. She’s so “cool,” that she’d call Ellen Page’s Juno a poser who sold out to a corrupted mainstream ideal of teen rebellion. When Enid and her equally non-chalant BFF Rebecca (Scarlett Johansson) see a missed connections ad in the classifieds (remember those, printed on actual paper?), they decide to pull a prank by setting up a date with the poster. What shows up is a shell of a man, a middle-aged dork named Seymour (Steve Buscemi) whose inherent sadness immediately attracts Enid. At first, she becomes friends with Seymour because of a hint of guilt, but eventually comes around to realize that she might have feelings for him. This scares her more than anything, since it also implies that maybe, just maybe, the perfect Ms. Enid, who’s above everyone else, might not be that different from this lovable weirdo who’s into collecting old Americana and blues records. Zwigoff and Clowes, together toeing the comic’s fine line between exaggerated cartoon characterizations and grounded regular people as protagonists, occupy Ghost World with eccentric people, to be sure, but people we all know well. Some of us even are those people. —Oktay Ege Kozak

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