Credit: Lucas Gouveia/How-To GeekIf you’re an HBO Max subscriber in the U.S., your queue is probably already busy as we wrap up June and leap over into July. House of the Dragon is lighting things up with season 3, finally making good on all those chess moves with the sizzling dragon warfare everyone wanted. And Larry David is off butchering American history for laughs just in time for the country’s 250th birthday. HBO Max is great at the headliners, but it’s the in-between nights that get you—the ones where you scroll forever before landing on a rerun.
With the Fourth of July weekend parked in there, here’s what’s worth a look from June 29 to July 5—a comedy heavyweight’s loose spin on the nation’s backstory, a wild reality series that sneaks up on you with some genuine moments, and one of those prestigious legacy titles—a foul-mouthed Western that earns every bit of its legend.
3
Life, Larry and the Pursuit of Unhappiness
Larry David crashes American history
Imagine Larry David’s ridiculously exaggerated Curb-style version of himself being dropped into the biggest moments in American history, and you pretty much get Life, Larry and the Pursuit of Unhappiness. And naturally, the hard-done-by, perpetually-annoyed comedy genius screws them all up.
This seven-episode HBO sketch series reunites David with his longtime Seinfeld and Curb Your Enthusiasm collaborator Jeff Schaffer for a loosely improvised romp across American history to mark the country’s 250th birthday. With each weekly half-hour episode packing in roughly four historical sketches, expect classic awkwardness, grievances, and more in what Richard Roeper at RogerEbert.com nailed by saying, “It’s not Drunk History, it’s Cnge History.”
Think Curb, but in costumes—David as a third Wright brother, as he’s wedged in the middle seat between Orville and Wilbur (Jon Hamm and Sean Hayes) during the brothers’ first flight (“I gotta sit in the middle with s****y snacks, for five hours?! Are you crazy?!”), or tagging along at Ford’s Theatre as Abraham and Mary Todd Lincoln (Bill Hader and Kathryn Hahn) try to enjoy a night out. Produced by Barack and Michelle Obama’s Higher Ground company, it features an impressive roster of guest stars, including Jerry Seinfeld, Isla Fisher, Vince Vaughn, and more. The first episode started streaming last Friday (June 26), with episodes dropping weekly through August 7.
Life, Larry and the Pursuit of Unhappiness
Release Date
June 26, 2026
Network
HBO
Showrunner
Jeff Schaffer
Cast
Larry David, Jon Hamm, Anna Osceola, Toby Huss, Lin-Manuel Miranda, Susie Essman, Jake Reiner, Emily McEnroe, Vince Vaughn, Isla Fisher, Bill Hader, Kathryn Hahn, Jane Krakowski
Directors
Jeff Schaffer
Writers
Jeff Schaffer, Larry David, Barack Obama
Main Genre
Comedy
Creator(s)
Larry David, Barack Obama
Producers
Jeff Schaffer, Larry David, Barack Obama, Michelle Obama
Seasons
1
Executive Producer(s)
Barack Obama, Ethan Lewis, Jeff Schaffer, Larry David, Michelle Obama, Vinnie Malhotra
2
Baylen Out Loud (season 3)
A wild and touching reality series about life with Tourette’s
I don’t like a lot of reality TV, but for all its “reality TV-ness,” at its heart, Baylen Out Loud is an earnest look at the life and challenges that people with Tourette syndrome endure. Now in its third season, which began streaming on HBO Max in late May, this TLC hit follows Baylen Dupree, a young woman living with severe Tourette syndrome, as she and fiancé Colin Dooley navigate one of the biggest stretches of their lives. Dupree built a massive TikTok following documenting her tics—including coprolalia, the involuntary outbursts of swearing, and often obscene words— and since its premiere season in 2025, the show grew into the most-watched new cable series of that year.
Season 3 centers on Baylen and Colin’s wedding planning, a possible cross-country move tied to Colin’s military career, and the usual family friction, with parents Julie and Allen weighing in throughout. Beyond the milestones, Baylen Out Loud has earned real credit for portraying day-to-day life with Tourette’s with honesty. Episodes continue each Wednesday (the day after they run on TLC) on HBO Max until July 15.
Network
TLC
Cast
Baylen Dupree
Main Genre
Reality
Seasons
3
1
Deadwood
HBO’s legendary frontier classic that more than holds up
As the month wraps up and the new releases thin out, I thought it would be a great time to include HBO’s legendary frontier classic that is still one of the best series the network, well, any network, has ever created. Set in the gold rush of 1876, the action in this acclaimed Western all happens in Deadwood, a dusty, lawless gold-mining camp in the Black Hills of South Dakota, as it lurches toward something trying to resemble civilization. And let’s just say it’s not going well.
The slow-burn power struggle pits Seth Bullock (Timothy Olyphant, Justified, Alien: Earth), a former lawman trying to run a hardware store and stay out of trouble, against Al Swearengen (Ian McShane, John Wick), the gleefully ruthless saloon owner who effectively runs the camp.
Deals
Score TV & streaming deals — big savings on home entertainment
Created by David Milch (NYPD Blue, True Detective), Deadwood gripped audiences (me included) with its intricate storylines and underhanded conflicts, but its real claim to fame was by far its dialogue that somehow blended gutter profanity with near-Shakespearean rhythm. The show was also known for threading real historical figures into the narrative—Wild Bill Hickok (Keith Carradine) and Calamity Jane (Robin Weigert) among them. Deadwood ran three seasons from 2004 to 2006 and wrapped with a 2019 reunion film. It garnered 28 Emmy nominations and scored eight wins, and it holds a 92% critics score on Rotten Tomatoes (should be 100%). If you haven’t seen it yet, now is the time.
Network
HBO Max
Cast
Timothy Olyphant, Ian McShane, Molly Parker, Jim Beaver, Brad Dourif, John Hawkes, Paula Malcomson, Leon Rippy, William Sanderson, Robin Weigert
Showrunner
David Milch
Writers
David Milch
Seasons
3
Streaming Service(s)
MAX
So long, June
However you spend the long weekend, this trio of HBO shows covers a lot of ground with something funny and apropos for Independence Day, a quirky and endearing reality show, and a classic that, ironically, also treads (if harshly) on the country’s early days. And if you want more where these came from, How-To Geek’s streaming roundups are stacked with picks across every major service.
Subscription with ads
Yes, $10.99/month
Simultaneous streams
2 or 4
HBO Max is a subscription-based streaming service offering content from HBO, Warner Bros., DC, and more. In 2025, the service re-branded itself as HBO Max after having previously cut “HBO” from its name.
Live TV
Live sports available in Standard and Premium plans
Price
Starting at $10.99/month or $109.99/year
