5 of the Best Shows on Showtime





Arming itself with a diverse lineup of programming, Showtime is quickly ascending the ranks of premium television channels. The network has some of the best shows on TV right now, and with creators like Lena Waithe and Paul Abbott leading Showtime’s creative charge, it’s easy to see why.

With so many critically acclaimed shows on the network, you might find it hard to figure out what you’ll watch next. There’s no right selection to make here, but to help you narrow down your choices, here are our top five shows on Showtime.

Related Reading: SHOWTIME: Free Trial, Deals, and Bundles

Black Monday

Don Cheadle and Regina Hall lead the ensemble cast of this comedy about the fake lives of Wall Street investors leading up to the very real Wall Street crash of 1987. It’s a show that portrays the workplace as a hostile and make or break type of environment. The first season follows an aspiring stockbroker who finds himself in a series of precarious situations when he joins a new firm and contends with hazing and overly competitive coworkers alike. The show depicts the worst stock market crash in US economic history through a Black lens, and introduces viewers to new perspectives as a result.

Why you should watch: The show doesn’t take itself too seriously, and frequently pokes fun at the very corporate, pack-like environment that exists in places like Wall Street.


Having run for 11 seasons, this drama about a family of impoverished siblings in Chicago who are forced to fend for themselves financially and often resort to some rather “unconventional” methods to do so is Showtime’s longest running show. The Gallagher family are at the center of this show, and the complex relationship the family has with one another, coupled with their absent, alcoholic father usually serve as fodder for the satirical commentary and one liners that make this show what it is. It’s described as a dark comedy by critics, and while its story lines aren’t always the most glamorous, it pairs tragedy with laughter, making concepts like poverty and survival palatable for the average viewer.

Why you should watch: It’s genuinely hilarious, and the actors rise to the challenge of making poverty funny without being insensitive or overtly problematic. It’s one of the few shows I’ve seen where all of the characters have a magnetism, and air about them that keeps you invested in their story and rooting for their success.

Desus and Mero

A late-night talk show comedy series featuring two podcast personalities whose episode topics run the gamut of everything from sports to pop culture. The hosts, Desus Nice and The Kid Mero, are known for their witty banter and unique perspectives on a range of topics, but viewers will be pleasantly surprised to find that the real star of the show is the “rainbow” featured on every episode. Each rainbow is personalized with a quote from the celebrity guest interviewed for the episode. The quotes are usually as random as they come; take Jimmy Fallon’s “Never compromise who you are as an artist for money, Toyota Let’s Go Places,” as a prime example. The show covers its fair share of serious topics as well, but does so with a light tone keeping it both fun and informative.

Why you should watch: It’s a fresh take on the late-night talk show genre. The hosts are hilarious, and celebrity guests are aspiring comedians in their own right, with snappy one liners and unexpected anecdotes that are so absurd you can’t help but laugh.


Jim Carey returns to the small screen with this surreal dark comedy about a children’s show personality reeling from a divorce and the passing of his son in a car accident. The premise, while grim, doesn’t fully encompass what this show is. It’s a story about dealing with grief in the public eye and the moments of reprieve that get us through life’s darkest moments. It’s funny, ironic, and allows Carey to showcase his range as an actor. Supporting storylines around adultery, dating after a divorce, and career changes add some more intrigue to this story as well. The show was recently canceled in July 2020, but 20 episodes and two seasons of Kidding are available on demand through Showtime.

Why you should watch: It’s a show that allows Carey to be everything we know him to be; eccentric, funny, and emotional. You’ll find episodes both heart-breaking and hilarious, and enjoy watching Carey’s character develop through the series.

The Chi

This drama takes place in the heart of Southern Chicago, and follows the lives of a cast of characters young and old. Their stories, while disparate, come together to give viewers a nuanced and more complete understanding of life on the South Side. Each of the shows three seasons hones in on a social problem centric to Chicago, with season one focusing on the murder of a teenager, season two dealing with grief and the drug trade, and season three beginning with the kidnapping of a young girl. It’s an ambitious show that’s trying to make several points by introducing you to various perspectives and problems that have no one right answer. 

Why you should watch: It’s a series that constantly reinvents itself story wise while managing to stay true to its foundation. The plots are complicated, never repetitive, and thought provoking.

There’s a lot to enjoy on Showtime if you’re into dramas or comedies. These are some of our recommendations to get you started on your next show binge.

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