2 seasons / 18 episodes
If you ask me, this is the single most underrated and underappreciated show on HBO. Laura Dern stars in writer/director Mike White’s darkly hilarious show about a woman whose every good intention goes horribly wrong. It only lasted two glorious seasons, probably because people had no idea what it was, but, hopefully, with the success of White’s latest masterpiece, The White Lotus, more may rediscover the lost gem that is Enlightened.
2 seasons / 18 episodes (so far)
I can’t recommend this show enough. I love it so much I keep recommending it to people I’ve already recommended it to—and nobody has been disappointed. The wickedly talented and far too unappreciated for far too long Jean Smart stars as Deborah Vance, a very famous but slightly has-been standup comic with a long-running Vegas show (think Joan Rivers). When Deborah’s boss starts to replace her with younger acts, she takes her agent’s advice and hires Ava (played by Hannah Einbinder), a young female writer to help boost her appeal to a younger demographic. You’ll be hooked by the hilarious dynamic between Deborah and Ava, but it will be Smart’s performance that will have you binging all day long.
SEX AND THE CITY (1998)
6 seasons / 94 episodes
Some shows are classics for a reason. Forget the films and all the real-life drama, when this show was on, nothing could beat it. Even though Sex and the City seems to be all about things I have no interest in like shoes, fashion, heterosexual relationships and New York City, I was absolutely addicted to it anyway, because it was just that good. From the delightfully witty writing to the four lead actresses who delivered the lines with panache, style, warmth and sass, Sex and the City is one of the finest comedy series of all time. If you’ve never seen it, or you’ve only seen the sanitized version on TV, you owe it to yourself to watch the real episodes (adult language very much included) on HBO and get Carrie-d away.
CURB YOUR ENTHUSIASM (2000)
11 seasons / 110 episodes (so far)
Larry David, the co-creator of Seinfeld, stars in a fictional show about a guy named Larry David who co-created Seinfeld. Yes, it’s all a bit bizarre, but David’s off-center way of looking at the world, along with his gaggle of famous and very funny friends make for a hilarious, mostly-improv show that keeps cringe comedy alive.
3 seasons / 24 episodes (so far)
Writer/producer Alec Berg, who executive produced and directed Silicon Valley, co-created another HBO show that I absolutely adore, Barry. Bill Hader co-created and stars in this dark comedy about a depressed hitman who falls in love with acting. That’s a really weird logline and of course the show is much more complex than that, but that’s the beauty of this show, it is weird, dark, traumatic, hilarious, goofy and deep. Hader proves he’s more than just the guy from Saturday Night Live (as proven by his 2 consecutive wins as Best Actor in a Comedy Series as the Emmys in 2018 and 2019), and surrounds himself with some of the best cast of characters on television, including Henry Winkler, Stephen Root and the revelation that is Anthony Carrigan, who steals every scene he’s in as the already-iconic NoHo Hank (who alone makes the whole show worth watching). I went on record saying that season 3 of Barry is the best season of television I’ve ever seen and I stick by it. If you can handle your comedy a little dark and twisted, Barry has to be at the top of your list.
7 seasons / 65 episodes
There’s a reason this show is at the top of nearly every “best of” list. It is pure perfection. Led by the iconic Julia Louis-Dreyfus in a career-defining role (and she played Elaine on Seinfeld), Veep is a satire of American politics so scathing, so bawdy and so scarily accurate it makes you wonder where reality stops and this show starts. This is not a sweet show, so buckle up your big boy/girl pants and prepare for foul language and lots of mean-spiritedness, but you’ll be massively rewarded by some of the best comedy writing of all time, delivered by an ensemble that clicks on all levels. And Louis-Dreyfus is nothing short of extraordinary, totally deserving of winning the Best Lead Actress in a Comedy Series six consecutive times, from 2012 to 2017.
OUR FLAG MEANS DEATH (2022)
1 season / 10 episodes (so far)
One of the true discoveries of the year, Our Flag Means Death is the perfect example of a show that completely grows on you. It starts slowly, but by the end of the season (so far, there’s only been one), you are desperate for more. If I tell you it’s a swashbuckling comedy about 18th century pirates, you may instantly think of Pirates of the Caribbean, and you wouldn’t be wrong, just adjust it to be even sillier, campier (if that’s possible) and much more heartfelt and you’ll get the best new show of the year. Rhys Darby, a New Zealand actor not too familiar to American audiences, steals the show, even away from Taika Waititi, who delivers his best acting performance yet (and also directs an episode). Give this gem a try and don’t give up on it after a slow and unpromising start. It will reward you for your patience, I promise.
SILICON VALLEY (2014)
6 seasons / 53 episodes
Writer/Producer/Director Mike Judge became famous by creating both the crude, low-brow animated series Beavis and Butthead as well as the somewhat less crude but still pretty low brow cult comedy film Office Space (of which I am admittedly a huge fan), but Silicon Valley is truly his masterpiece. A comedy series about the digital age and the dorky geniuses that changed the world, Silicon Valley features some of the best comedy television has to offer, brutal and searing at times, sweet and nerdy at others, but always witty and timely. If you’ve ever wondered what life was like behind the digital curtain of your favorite software programs, apps or computers, let Silicon Valley give all the (fictional) Zuckerbergs and Bezos’s their just desserts. The only negative of the show is the star, Thomas Middleditch, has as much appeal as a wet dishrag, but it says a lot about the show that there are so many other elements to this show to more than make up for his shortcomings.
6 seasons / 62 episodes
Say what you want about Lena Dunham now, but her show Girls was a refreshing, engaging and raw look at young adults in New York. It was a perfect show for its moment and it seized it. Dunham’s voice was unaffected, honest and presented the female experience in a way not often seen, a Sex and the City for a new generation. It is uncensored and revels in its sexual experiences and off-color language, but if you can handle that, this show is a gem. Bonus points for discovering Adam Driver, who, despite all his fame and roles since, has never been better than he was in this.
TRACEY TAKES ON… (1996)
4 seasons / 48 episodes
TRACEY ULLMAN’S SHOW (2016)
3 seasons / 19 episodes
The genius comic chameleon Tracey Ullman has two masterpieces of sketch comedy on HBO, each one worth savoring.
HELLO LADIES (2013)
1 season / 8 episodes and 1 movie
Nobody talks about this one, but it is a charming one-season series starring Stephen Merchant as a pathetic and somewhat dorky Englishman trying to find love (or at least some dates) in Los Angeles. While you may not know Merchant’s name or face, you definitely know his wit, as he co-created popular shows The Office, Extras and Lip Sync Battle, among others. As an actor, Merchant is adorably effacing (thanks to being 6’ 7”) and is at his best when he lets his confidence run away with him, as it does often in this very sweet and engaging romantic comedy series. The show does end abruptly, as I’m sure they were expecting a second season, but they did make a movie to wrap things up, which is charming as well.