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Hello, and welcome back to Comedy Means Business.

Have a stacked newsletter for you today, leading off with a Q&A with Jeff Ross – on the awards circuit with the Netflix capture of his debut Broadway show Take a Banana for the Ride. A career highlight that he feels helped cure him of stage 3 cancer.

On the news front, I have intel on an 800 Pound Gorilla deal with Comedy Central Records, a New York’s Funniest Stand Ups showcase to take place at Southampton Playhouse, Willie Macc's debut special, and new tour dates for Rosebud Baker, who just unveiled memoir Fully Baked.

In this edition, we also have a new special of the month, and I introduce Back of the Room, a new segment from NY-based comic Matt Ruby, where he shares an eclectic array of thoughts on the comedy business.

ICYMI, this past week, Sarah Sherman joined the Comedy Means Business podcast to discuss her maximalist HBO special Sarah Squirm: Live + in the Flesh, awkward SNL dynamics, bombing like Oppenheimer, and more. You can watch that here. Up next: Eric André.

Now, let’s get into the newsletter.

THE DEADLINE Q&A

JEFF ROSS

Jeff Ross in Take a Banana for the Ride (courtesy Netflix)

In the fall of 2024, after a routine colonoscopy, comedian Jeff Ross received an unexpected diagnosis: He had Stage 3 colon cancer and would need to undergo surgery to remove seven inches of his colon, followed by six months of chemotherapy.

It's the sort of revelation that would lead most people, understandably, to panic and shut down. But not the Roastmaster General, who less than a year later, would mine the experience with Take a Banana for the Ride, a deeply personal one-man show marking both his Broadway debut and the coalescing of a lifelong dream.

Ross' show takes its name from a cherished piece of advice given to him by Pop Jack, his late, beloved grandfather, with whom he lived while starting out as a comic. It's a portrait of resilience in the face of loss and life's other challenges, explaining the role humor has played in helping Ross to navigate it all.

Over the course of 90 minutes — a tribute to the people that made him, taped as a special for Netflix, which is now up for Emmy consideration — Ross doles out his life story, in hopes that it will help others, delving into the history of his New Jersey family, his origins as a comic, and how he's dealt with not only the early loss of his parents, but also that of a trio of comedy superstar pals (Bob Saget, Gilbert Gottfried, Norm McDonald), one of his beloved dogs, and more.

Backed by a set of gold frames that he uses to pull up images from his past, Ross is dressed in a banana-yellow suit and concludes his show by handing out bananas to strangers dealing with their own battles, as a sign of camaraderie and token of his appreciation.

In an interview with Deadline, Ross breaks down his journey with a show which he first began touring in the '90s, which took its full form decades later. He reflects on the emotion summoned by a show he equates to "digging up my parents" and how he learned to conquer it, also sharing how advice from Jim Carrey on manifesting led him to pursue Broadway full force.

Amid his "career-defining moment" with Take a Banana for the Ride, which he believes helped "cure" him of cancer, Ross also discusses why Kevin Hart "deserves a Nobel Peace Prize" for taking the hot seat at this year's Netflix roast, the evolution of the art form from the days of Comedy Central's roasts, and the prospect of more seasons of his Netflix stand-up series Bumping Mics.

Read the Q&A here.

THE DEADLINE EXCLUSIVE - #1

SOUTHAMPTON PLAYHOUSE PARTNERS WITH CAROLINE HIRSCH TO PRESENT NEW YORK’S FUNNIEST STAND UPS

L-R Jason Choi, Jaye McBride, and Maddy Smith (courtesy New York Comedy Festival)

NEWSLETTER-ONLY EXCLUSIVE: The Southampton Playhouse has partnered with Caroline Hirsch — founder of Carolines on Broadway and the New York Comedy Festival — to bring the showcase New York’s Funniest Stand Ups to the East End.

Taking place on Tuesday, July 7 at 7:00 PM at the Southampton Playhouse in Southampton, New York, the event will feature performances by Jason Choi, Jaye McBride, and Maddy Smith — a trio who participated in New York’s Funniest Stand Ups during the 2025 New York Comedy Festival.

“One of the greatest privileges I’ve had in my career is having a front-row seat to the incredible new voices shaping the future of comedy,” said Hirsch, who is on the Advisory Board of the Southampton Playhouse. "We've helped introduce audiences to performers who went on to become household names, and we're always looking for the next breakout star. We're thrilled to partner with the Southampton Playhouse to bring some of New York City's most exciting emerging comedians to the Hamptons.”

Maria A. Ruiz Botsacos, Executive Director of the Southampton Playhouse, said: "Caroline’s influence in the comedy space is truly unmatched and we are thrilled she has chosen to partner with the Southampton Playhouse for this exciting event. She has curated a dynamic group of comics and we are thrilled to welcome them to the East End for this memorable evening.”

Since originating at the New York Comedy Festival in the late 2000s, New York’s Funniest Stand Ups has proven a premier breeding ground for top young talent, having helped launch the careers of comics including Nate Bargatze, Michael Che, Jordan Jensen, Tim Dillon, Josh Johnson, and Ricky Velez. For more information and to purchase tickets, visit this link.

THE DEADLINE EXCLUSIVE - #2

800 POUND GORILLA EXPANDS FOOTPRINT VIA COMEDY CENTRAL RECORDS DISTRIBUTION DEAL

NEWSLETTER-ONLY EXCLUSIVE: 800 Pound Gorilla has inked a deal to become the official audio distributor for Comedy Central Records, expanding the roster of acclaimed comedy talent under its umbrella. The deal brings together catalogs from comedians including Nate Bargatze, Jim Gaffigan, Amy Schumer, Aziz Ansari, Patton Oswalt, Big Jay Oakerson, Kyle Kinane, Mark Normand, Sam Morril and many more.

The idea, in consolidating these fan-favorite releases into a single distribution ecosystem, is to strengthen discoverability, streaming reach, and long-term audience engagement for some of modern comedy’s most recognizable voices while reinforcing 800 Pound Gorilla’s role as a leading force in comedy production, distribution, and digital media. Already, the company has struck similar partnerships with Kevin Hart’s Laugh Out Loud Network, Nate Bargatze’s Nateland Entertainment, and All Things Comedy.

800PG co-founder Damion Greiman, told us, “Comedy Central's stand-up catalog is legendary, and we are excited to bring it to the next generation of stand-up comedy fans.”

Co-founder Ryan Bitzer added, “Bringing Comedy Central into 800 Pound Gorilla's family has been a goal of the company since the beginning. With over 60% of stand-up audio being distributed through this team, we can now bring together the catalogues of the most notable names in comedy.”

With a combined 3.1M followers and reaching over 20 million comedy fans a month, 800 Pound Gorilla celebrates its 10th anniversary at Just for Laughs Montreal this summer.

THE DEADLINE EXCLUSIVE - #3

WILLIE MAC SETS RELEASE PLANS FOR SPECIAL 'GOOD DAD, BAD FATHER'

Willie Macc in Good Dad, Bad Father (courtesy 800 Pound Gorilla)

NEWSLETTER-ONLY EXCLUSIVE: Comedian Willie Macc has announced that his first full-length special, Good Dad, Bad Father, will stream exclusively on Gorilla Comedy+ beginning June 22 before heading to YouTube on July 21.

Macc’s show is about becoming a dad before fully becoming an adult.

"My dad raised me with scripture. I raised my son with vibes. Good Dad, Bad Father is my commentary on the gap between the two,” the comedian told Deadline. "It's about fatherhood, church trauma, growing up Southern, dating, mental health, ADHD, trying to be a good man and realizing that sometimes you can love your kid and still have no idea what you're doing.”

Macc taped the special, produced by Super Nice Guys, at The Kookaburra Lounge in Hollywood. Upcoming, he’s set to release another new special, Dad, Grandmas, and Bears, Oh My, with Dry Bar Comedy.

Macc’s comedy has been showcased by Don't Tell Comedy, Netflix Is a Joke, Comics Unleashed, TruTV’s Laff Mobb’s LaffTracks, and across social media to over 100 million views. He hosts the podcast Afronoodles and has also appeared on shows like Snowfall, CSI, Casual and The Goldbergs. Additional credits include HGTV’s My Flipping Family and comedy Meet the Spartans with Kevin Sorbo, Carmen Electra and Tiffany Haddish. He is repped by Arsonhouse Entertainment.

THE DEADLINE EXCLUSIVE - #4

Rosebud Baker Sets New Tour Dates

NEWSLETTER-ONLY EXCLUSIVE: Following the June 9 launch of her memoir, Fully Baked, Rosebud Baker has unveiled new tour dates exclusively with Deadline, which you can view below.

Baker is a comedian, actor, and Emmy-nominated writer who worked on staff at Saturday Night Live from 2022 to 2025. She has also written and performed on the WGA Award–nominated That Damn Michael Che and Inside Amy Schumer, winning for her work on the latter. Baker's debut stand-up special Whiskey Fists, produced by Bill Burr and All Things Comedy, premiered on YouTube in 2021. More recently, she took to Netflix with the hour The Mother Lode.

Inspired by her pregnancy and early motherhood, Baker’s Fully Baked is part of her quest to discover who she really is and how she wants to raise her kid. No subject in her life is off limits, from her famous yet unknowable grandfather, White House Chief of Staff James A. Baker III, to her youngest sister’s sudden death.

Baker is also known for acting work in Life & Beth on Hulu and the horror-comedy Hell of a Summer. Based in New York, she is repped by Brillstein and UTA.

June 19, 2026 — OPENING FOR JON STEWART: Hartford, CT - Bushnell PAC Mortensen Hall

June 20, 2026 — OPENING FOR JON STEWART: Sat. 6/20 - Lennox, MA - Tanglewood

July 10–11, 2026 — Las Vegas, NV — Wiseguys Town Square

July 30–Aug 1, 2026 — Burlington, VT — Vermont Comedy Club

Aug 14–16, 2026 — Washington, DC — DC Improv Comedy Club

Sept 18, 2026 — New York, NY — Gramercy Theatre

Sept 24–26, 2026 — Baltimore, MD — The Port Comedy Club

Oct 16–17, 2026 — Dallas, TX — Dallas Comedy Club

Oct 23–24, 2026 — Nashville, TN — The Lab at Zanies

Nov 5–7, 2026 — Tacoma, WA — Super Funny Comedy Club

Nov 13-14 2026 - Toronto, ON — Toronto Comedy Bar

Dec 5, 2026 — Somerville, MA — Crystal Ballroom at Somerville Theatre

BACK OF THE ROOM

Matt Ruby Muses On AI, Kevin Hart Roast, Roy Wood Jr.'s Comedy Wisdom & More

Matt Ruby (courtesy Sam Cashell)

• AI will be great at writing monologue jokes and bad at doing depthful standup because the former is baby-food-ish formulas that gently soothe and the other is based on presenting a unique pov that delivers slap-in-the-face surprise.

• The Kevin Hart Roast: Of course there was online backlash. Social media loves to ignore context and intention so a comedy roast is its natural enemy. All the fighting about it feels like watching a bunch of wrestling fans who think kayfabe is real.

• There's a big reason why social media and standup are so often at odds. Social media performance is all about tribalism, fixed ideology, and moral superiority. Standup performance is (frequently) about attacking tribalism, shapeshifting toward whatever gets a laugh, and pointing fingers at everyone (including yourself).

• Brick walls being considered funny is some real Pavlovian stuff.

• Used to be the goal of a comedian was to do either five minutes or 30 minutes. That’s how you got ahead. Now, you gotta do either 30 seconds or three hours.

• Right now someone’s posting a video of a chihuahua and a penguin becoming friends and every comedian is supposed to write a joke that’s more entertaining than that. Tough assignment.

• Comedy: “Wait for it.”
The attention economy: “I refuse to wait.”

• Ram Dass = "Be here now." Comedy = "You had to be there." Feels like proof mindfulness is the essence of comedy. If you want to laugh, be there now.

• If you want to learn about doing standup comedy, find every Roy Wood Jr. interview you can (tons of good pods with him avail). Not only is he as good as it gets onstage, no one is more eloquent on the subject.

• Standup comedians went from hating on improv to doing it constantly but just calling it crowdwork and podcasting.

• Crowdwork: I couldn’t care less what people in the crowd do for a living or how long they’ve been dating. I chose to do standup because I think my ideas are more interesting than Dave in accounting. If I wanted to make insincere small talk with some boring bro, I’d work in a cubicle.

• I’m convinced crowdwork clips do well because shut-ins are fascinated by two strangers having an actual conversation. "They don't even know each other and they're talking!? Wow! What’s that like?"

• Now: Cisgender females frequently respond to the systemic oppression of late-stage capitalism by overindexing on consumerism.
Then: Women be shoppin’.

• Sketch idea: Subway Takes from a century ago. So it’s the 1920’s and it’s Horse-Drawn Carriage Takes and the person holds a megaphone while shouting opinions like “Flappers have weird haircuts.”

• Turns out the only thing worse than making art requiring the approval of network executives is making it for soulless algorithms controlled by venture capitalists.

• Everyone keeps trying to do comedy shows in places that are not made for comedy which is confusing because people built rooms ideally suited for standup (i.e. comedy clubs). It's like if everyone decided it'd be an "immersive experience" if the NBA played basketball games at a deli.

• Walter White doing comedy: “I am the one who knock knocks!”

Back of the Room is a collection of thoughts on comedy from Matt Ruby, NYC comedian, writer, and the author of Funny How: Letters to a Young Comedian (a newsletter about the craft of standup for comedians, industry types, and anyone else who’s a comedy nerd).

SPECIAL OF THE MONTH: MAY

Josh Johnson: Symphony

Josh Johnson in Symphony (courtesy HBO)

This round goes to Josh Johnson for his excellent HBO special, Symphony — an hour Deadline was first to report on, which premiered on May 22. Symphony is Johnson’s third special on the heels of #(Hashtag) (Comedy Central) and Up Here Killing Myself (Peacock) and marks a new creative chapter for the comic, as he discusses in an upcoming episode of Deadline's Comedy Means Business podcast.

Shot at The Wiltern, the special is, unlike most, an experience — visually elegant and surprising, with memorable vignettes on everything from a childhood karate nemesis to eating with his weird uncle.

Love this opening quote riffing on Basquiat: "If art is how we decorate space and music is how we decorate time, comedy is how we decorate reality."

If there’s any young stand-up who can hope to break into a show like the Emmys — whose stand-up categories are generally dominated by A-listers like Ricky Gervais, whether the specials nominated are exceptional or not — I believe it’s Johnson. He’s a pretty unique character, as someone with an established platform like The Daily Show behind him, who at the same time, has actually built his powerful touring business on the back of his YouTube presence.

Deciding on the month’s best special is always the most difficult thing with this newsletter — there’s so much good work out there that it’s inevitably a tough call.

Honorable mentions this month go to veteran Daily Show scribe Matt Koff for Cat Man (covering black-tie lesbians, socially awkward Jewish men, and pregnancy scares); Jim Carrey lookalike Heather Shaw’s Alright, See Ya! (riffing on being misgendered and being able to count all the teeth in the room while doing a show in Omaha); and Gabriel Rutledge, whose A Reasonable Hour is an outright banger, with jokes on yarn-eating cats, older people’s love of “activities,” and being called a fat Dave Grohl.

All three of the latter specials went straight to YouTube, where you can find so many of today's best. N.B.: Rutledge appears to be unrepped. Check out the specials from Koff, Shaw, and Rutledge at the links above.