3 of the best specials from Boston comedians streaming now

Round 1 of our Best Boston Comedian bracket is in the books, and I think some readers are going to be quite shocked.

A pair of 2-seeds – Jennifer Coolidge and Jay Leno – were upset by two 7-seeds thanks to some personal lobbying from one comedian. And one of the 1-seeds – Bill Burr – barely eked out a victory.

The second round of voting is now open, and the matchups only get harder from here. But before we forget about the 16 funny folks who exited stage left, I’d like to highlight some of their best material.

Along with the usual weekly streaming recs, this week’s edition of The Queue has a quick recap of our ongoing comedy bracket, as well as three specials worth watching from local comedians who readers voted off the island.

If you want to see the full results from Round 1, scroll to the bottom of our landing page. Round 2 voting is now open through Monday afternoon.

Biggest upset: 7-seed Sam Reich (56.6%) over 2-seed Jennifer Coolidge (43.4%)

Not only did the Cambridge native post on social media about his matchup against Coolidge, he also rallied around fellow 7-seed (and Dropout regular) Pete Holmes, who took down former “Tonight Show” host Jay Leno. Will this “bad b****” (to use Reich’s words) have what it takes to beat Matt LeBlanc in Round 2? Sam says yes.

Closest call: 1-seed Bill Burr (50.4%) over 8-seed Paula Poundstone (49.6%)

Though I knew Paula Poundstone had plenty of fans from her decades of standup and NPR appearances, I did not anticipate that she would finish within tenths of a percentage of Bill Burr.

Toughest decision: 4-seed Jenny Slate (39.3%) vs. 5-seed Jason Mantzoukas (60.7%)

For fans of “The Office,” picking between Mindy Kaling and B.J. Novak was probably the hardest. But for me, it was Slate vs. Mantzoukas, two longtime collaborators on shows like “Big Mouth,” “Kroll Show,” and “Parks & Recreation.” In the end, online support from listeners of the Comedy Bang Bang and How Did This Get Made podcasts likely helped Zouks over the line.

Given how many comedians from the Bay State didn’t even make our field of 32 comics, those who lost in Round 1 shouldn’t feel discouraged. But as a parting gift, here are three specials from the list of losers streaming now.

“Gary Gulman: Born on Third Base” (2023)

The Peabody native gained greater recognition for 2019’s “The Great Depresh,” an honest examination of his lifelong struggle with depression. Gulman’s newest special is closer to his typical style of observational comedy, with a particular focus on the haves and have-nots. (HBO Max)

“Jenny Slate: Stage Fright” (2019)

Slate emphasizes the local in her debut special, which blends traditional stand-up with documentary footage from her childhood home and stories of growing up in Milton. (Netflix)

“Chris Fleming: Live at the Palace” (2026)

Executive produced by Conan O’Brien (Fleming’s opponent in our bracket), the Stow native’s HBO special showcases Fleming’s boundless energy and skewed outlook on the world. (HBO Max)

Play or Skip

Have a show you can’t stop watching? Email me about it at [email protected], and your recommendation may appear in a future edition of The Queue.

Press play on these new movies and shows:

“The Invite” (2026)

Speaking of local performers, Olivia Wilde told me about how her time at Phillips Academy in Andover helped inform her work directing “The Invite,” a darkly funny film that functions more like a stage play. Wilde and Seth Rogen play a couple who should’ve divorced years ago hosting the upstairs neighbors (Edward Norton, Penelope Cruz) for a dinner party that takes a turn. (HBO Max)

“The Dropout” (2022)

First, you should get off your couch and head to the theaters for “You Can See Everything.” One of the best movies of 2026, the mind-bending documentary is nominally about Theranos founder Elizabeth Holmes, who welcomed comedian Nathan Fielder into her home right before she went to prison in 2023. Without spoiling the film, I’ll just say that watching this 2022 miniseries, which stars Amanda Seyfried as the disgraced tech mogul, is an edifying experience. (Hulu)

“Nobody Wants This” Season 3 (2026)

Kristen Bell and Adam Brody’s interfaith odd couple have moved in together in Season 3, leading to a season that is mostly light and pleasant but with enough drama on the margins to keep us entertained. (Netflix)

But go ahead and skip this one:

“The Terminal List” Season 2 (2026)

Four years after its first season, Chris Pratt’s Navy SEAL commander is back, and he’s bent on revenge (due to events from Season 1 that I won’t spoil). The new season is passable, but it’s hard to match the show’s emotions after such a long layoff. (Prime Video)