Regina Hall and Don Cheadle parody 1980s Wall Street in “Black Monday” on Showtime. And “High Maintenance” returns for a third season on HBO.
What’s on TV
BLACK MONDAY 10 p.m. on Showtime. The cocaine flows and the cash is blown in Showtime’s claustrophobic new half-hour comedy series, which dresses Regina Hall and Don Cheadle up in 1980s garb and attempts to bottle the trembling energy of a B-level Wall Street brokerage firm operating on the brink of a stock market crash. Cheadle plays Maurice Monroe, the head of the firm, who delights in riding in a Lamborghini limousine and whose response when presented with a bag of cocaine as a birthday gift in the first episode is to say, “You guys get me.” Dawn Darcy, played by Hall, is an expert trader; Andrew Rannells plays an eggheaded Wall Street newcomer.
CRASHING 10 p.m. on HBO. Following in the footsteps of shows like “Seinfeld” and “Mulaney,” this big-hearted comedy series features the stand-up comic Pete Holmes playing a version of himself. When the series picked up, Holmes’s character was spat out of a crumbling marriage and into the New York comedy scene. In the third season, debuting Sunday night, his character — a spiritual comedian — is returning to the city from a college comedy tour and plunging into a new romance. “While I love ‘Louie,’ and ‘Seinfeld,’ those are about successful comedians,” Holmes told The New York Times in 2017. “We’re telling a story of what it’s like to hand out fliers in exchange for stage time at 1 in the morning at a club for five people. And that’s such richer kind of tapestry to explore.”
HIGH MAINTENANCE 10:30 p.m. on HBO. With the legalization of marijuana in New York State seemingly on the brink of becoming a reality, how will “The Guy” — the pot dealer and only constant character in Katja Blichfeld and Ben Sinclair’s exploration of the lives of fictional New Yorkers — maintain his livelihood? The debut episode of the show’s third season on HBO (it started out as a Vimeo web series) offers what could be viewed as a glimpse: The Guy (Sinclair) doesn’t sell anything. Instead, the multithreaded episode follows the aftermath of a death in upstate New York. As a friend of the deceased (Erin Markey) copes with grief by eating onion pizza and drinking craft beer, a new romance is born when The Guy meets a local soul (Britt Lower).
STAR TREK: DISCOVERY streaming on CBS All Access. CBS’s “Star Trek” prequel series has made two important changes in its second season: tighter plot structuring and the addition of the comedian Tig Notaro, who plays a heroic officer. The new season’s debut episode, Sopan Deb wrote in The Times, “has everything that the best episodes of ‘Trek’ have historically had: a mystery, excellent ensemble work with a genuine sense of camaraderie, action scenes that don’t overwhelm the plot and most importantly, genuine fun.” It also features the show’s flagship ship, the Enterprise, remade with current-day graphics.