Jinkx Monsoon is a comedian and singer best known for becoming the first performer to win two seasons of RuPaul’s Drag Race, first in season 5 in 2013, followed by the all-winner all-star edition in 2022, where she was crowned “Queen of All Queens.” She began touring annually over the holidays in 2018 with fellow Drag Race star BenDeLaCreme, and you can watch The Jinkx & DeLa Holiday Special on Hulu. Jinkx has released multiple albums, been the subject of two documentaries, and has appeared on TV shows such as Blue Bloods and AJ and the Queen. In 2022, Jinkx filmed her first solo comedy special for Comedy Dynamics at the Tribeca Film Festival, and is the creator, writer and star of the sketch comedy series, Sketchy Queens, debuting on WOWPresents Plus in September 2022. Jinkx joined me over Zoom to talk about the evolution of her life and career, and what comes next.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Michelle Ortiz was born in Los Angeles but studied all over the world, including the Moscow Art Theatre School, and classical opera in Germany. A participant in both the ABC and CBS diversity showcases, Ortiz broke through first as a cast member on the reboot of MADtv for The CW — where she impersonated the likes of Kim Kardashian, Melania Trump, Sofia Vergara, Jennifer Lopez, and Dora the Explorer. Ortiz also has appeared on I Think You Should Leave with Tim Robinson, Mom, Life in Pieces, Gentefied, and When Nature Calls with Helen Mirren. In 2022, Ortiz has a new chance to shine as Maggie in the Hulu comedy series, This Fool. Ortiz sat down with me to discuss how she found her way in the world and in comedy.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Alice Fraser first studied law in Sydney, Australia, but found comedy and the Footlights while getting her Master’s degree in rhetoric at Cambridge, and honed her stand-up skills in New York City’s open mics and comedy clubs before returning to Australia as a comedian. You’ve likely heard Fraser’s voice before if you’re a fan of The Bugle. She also hosts a weekly spin-off podcast, The Gargle — and in the first year of the COVID pandemic, she wrote and performed a daily satirical news podcast, The Last Post, set in an alternate dimension. She’s also co-hosted best-selling documentary audiobooks on Audible, and her 2020 stand-up special, Savage, was released as an Amazon Original on Prime Video. Fraser sat down with me between shows in her 2022 Edinburgh Fringe run of her latest hour, Chronos. We had an enjoyable and educational discussion about the harsh economics of stand-up comedy, whether you’re taking your show to the Fringe or just trying to pay the bills and support a family.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
The creator and star of HBO’s “A Black Lady Sketch Show,” Robin Thede and her crew already have enjoyed 13 Emmy nominations and one Emmy win heading into the 2022 awards ceremony, as well as 2020 honors from the TV Critics Association for outstanding sketch/variety series. Thede grew up in Iowa, studied broadcast media at Northwestern and made a brief stop at The Second City before going Hollywood. She scored supporting roles in short-lived sketch shows for Mike Epps and Affion Crockett, but much of Thede’s early success came behind the camera as a writer — for the BET Awards, Real Husbands of Hollywood and The Queen Latifah Show. Thede broke through as the first black woman to serve as head writer in late-night TV for The Nightly Show with Larry Wilmore, then got her own late-night show, The Rundown, on BET. When that show abruptly ended, it opened the door for Thede to take her talents to HBO, where she not only has shone brightly, but also helped pave the way for success with past and present fellow castmates such as Quinta Brunson and Ashley Nicole Black. Thede sat with me to talk about all of that and more.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Brian McElhaney and Nick Kocher grew up near each other in Atlanta but only became a sketch comedy duo while attending NYU together. As BriTANicK, they’ve made viral videos for YouTube, Cracked, CollegeHumor and Funny or Die, catapulting them onto Variety’s 10 Comics to Watch list in 2013. They’ve acted together How I Met Your Mother, Much Ado About Nothing, and the indie comedy film Balls Out; they’ve written together for Saturday Night Live, as well as It’s Always Sunny in Philadelphia, and The Goodwin Games. They’ve been the voices of the Cartoon Network. And now in the summer of 2022, 14 years after they first took to the comedy stages of New York City, they’re back performing live once more, taking their best sketches to the Edinburgh Fringe festival. But first, they sat with me to talk about their journey.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Originally from New Jersey, Anthony DeVito is a NYC-based comedian who has performed on The Late Show with Stephen Colbert, released a half-hour special on Comedy Central, and a full special, “Brain Noise,” in May 2022 on YouTube. DeVito was a writer and sidekick of Sam Morril on MSG's People Talking Sports and Other Stuff. He followed that up by writing for Netflix’s The Break with Michelle Wolf, which also led him to writing jokes for Wolf when she delivered the keynote at the 2018 White House Correspondents Dinner. You may have heard him talking about his relationship with his grandmother on This American Life, but you may not yet have seen or heard his one-man show, “My Dad Isn’t Danny DeVito.” He’s taking that show to the 2022 Edinburgh Fringe festival. But first, he sat with me to discuss his life and career.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Emily Wilson is a comedian and actress based in New York City who performs stand-up, characters and funny songs. Wilson hosts a weekly comedy showcase in the East Village called Tuesdays at the Red Room. But you may have seen her before and not realized it — Wilson competed on The X Factor in 2011, when she was only 15 — and that experience is mined for her one-woman show “FIXED,” which she is taking to the Edinburgh Fringe Festival in 2022. Before that, though, Wilson sat down with me to talk about what happened after The X Factor and how it’s formed her as a person and as a performer.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Lance Reddick stars as Renzo, an egotistical human warrior who has liberated the planet Farzar from evil aliens — it’s all part of the new Netflix sci-fi animated comedy series, Farzar, created by Roger Black and Waco O’Guin, whose previous animated projects include Brickleberry and Paradise PD. Black and O’Guin have been making outrageous comedy since meeting in college at the University of Georgia, and I spoke with them about their journey from Yucko The Clown on Howard Stern to animation, and with Reddick about pivoting from prestige TV to prank comedy.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Kylie Brakeman is an actress and comedian who broke through during the pandemic, as millions have found themselves laughing and sharing her videos where she faces the camera as one of many high-energy characters just trying to make sense of the world we live in now. From the strength of her videos on Twitter, Instagram and TikTok, Brakeman has landed writing jobs on Peacock’s The Kids Tonight Show, as well as the Discovery Plus series Kicking & Streaming. Brakeman is showcasing her character live and in person at the 2022 Edinburgh Fringe Festival with Kylie Brakeman Presents: Linda Hollywood’s Big Hollywood Night. But first, she sat with me to talk about her life and career thus far.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
The daughter of Jamaican immigrants, Jackie Fabulous grew up in The Bronx but went to law school in Southern California before deciding in her mid-30s to pursue a career in stand-up comedy. After some initial TV credits on Arsenio and Last Comic Standing, her comedy path began to become truly fabulous after she competed on America’s Got Talent in 2019. She moved back to The Bronx just before the pandemic, and since then has performed twice on The Tonight Show, booked gigs on Showtime’s Flatbush Misdemeanors and HBO’s That Damn Michael Che, and recorded her first hour-long stand-up special, Menoplause, released in July 2022 via Comedy Dynamics. Fabulous joined me over Zoom to talk about her life and career.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Jordy Fox Ellner is the head of film, TV and podcast development at All Things Comedy, the production company launched by comedians Bill Burr and Al Madrigal. Ellner started as a comedian himself in the late 1990s in Los Angeles, where Mitzi Shore made him a doorman and eventually a paid regular at The Comedy Store. His career transitioned in 2006 when he took over the fledgling comedy division at MySpace, and when that platform fell out of favor, he found refuge at Jokes.com and Atom.com, which eventually led him into the fold at Comedy Central, where he rose to become VP of talent and development before leaving in 2020 to join All Things Comedy.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Dan Perlman started out as an intern on SiriusXM’s “Ron and Fez Show” and continued working with and for Ron Bennington while he was hitting the stand-up open mic scene in New York City. After winning the Just for Laughs-New York TV Festival’s "Set to Screen" Comedy Pitch Competition in 2015, Perlman earned himself a pilot presentation from FOX for his animated project, That’s My Bus. But it was his web videos with fellow comedian Kevin Iso, which started out as “Moderately Funny,” and eventually evolved into what we know as Flatbush Misdemeanors, the Showtime series Perlman co-created, executive produces, writes and stars in — Perlman sat down with me before the second-season premiere to talk about making videos without worrying if they go viral, making sure everyone from the web series had a role in making the TV show, and more.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Iain Stirling’s Scottish accent might be known around the world for narrating the exploits of the hit British reality TV series, Love Island. But in Stirling’s first Amazon Original stand-up special, Failing Upwards, the comedian finds himself falling short of everyone else’s expectations when it comes to his physical health and his love life. Stirling sat down with me over Zoom to discuss how growing up in Edinburgh sparked his early comedy career, the realities of working with his wife in reality TV, and why he wanted to make sure his comedy special for Amazon was truly special.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
You may have heard Helen Hong as a regular panelist on the hit NPR quiz show, “Wait Wait…Don’t Tell Me.” Hong also has appeared on the big screen in Inside Llewyn Davis, and in recurring roles on TV in sitcoms and comedy shows including HBO’s Silicon Valley, The Unicorn on CBS, and The Netflix Afterparty. And as a stand-up comedian, Hong has grown up from her start as a “Little Ethnic Girl,” releasing her debut comedy special, Helen Hong: Well Hong, via Comedy Dynamics, which she recorded in the summer of 2021 as part of the Tribeca Film Festival. Hong sat down with me over Zoom to talk about her early days and nights as a TV producer behind the camera, how she moved to Hollywood without a steady gig and lived to joke about it, filming a nationwide TV commercial with a Muppet, and her life as the daughter of Korean immigrants.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Wyatt Cenac and Donwill have enjoyed a long friendship and working relationship, with the DJ providing beats and sidekick commentary for Cenac when he had a long-running Monday night stand-up showcase in Brooklyn called Night Train, which begat a Seeso series of the same name. They also worked together on HBO’s Problem Areas with Wyatt Cenac. And since 2011, the duo has presided over a live movie screening event called “Shouting at the Screen,” in which they provide running commentary and more while watching a classic blaxploitation film. After hitting pause for two years during the pandemic, they have relaunched Shouting at the Screen at a new location in Prospect Park. Cenac and Donwill joined me over Zoom to talk about their comedy collaborations, the joys of guiding audiences through cinematic experiences, and how to balance jokes and silly ideas with weighty subject matter.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Bruce McCulloch is a Canadian actor, writer, and director best known as one of the five Kids in the Hall — who came back in a big way in 2022 — their sixth season of sketch comedy premiered May 13 on Amazon Prime Video, with a documentary about them, Kids in the Hall: Comedy Punks, out the following week. As a solo act, McCulloch has written a book (“Let’s Start A Riot”), released two albums, Shame-based Man and The Drunk Baby Project, and created the sitcom Carpoolers for ABC. He’s also directed movies such as Superstar and Stealing Harvard, as well as shows such as Brooklyn Nine-Nine, Schitt’s Creek, and Trailer Park Boys, and he has shepherded a new Canadian sketch comedy group, TallBoyz, to TV on CBC and Fuse. His latest one-man show, “Tales of Bravery and Stupidity,” will make its off-Broadway debut in June 2022 at SoHo Playhouse. McCulloch invited me to his hotel room to talk about the makings of The Kids In The Hall, and his perspective on it all.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Addie Weyrich got an early jump on her comedy career, dropping out of NYU when the teenager’s work with the likes of the Upright Citizens Brigade, Improv Everywhere and Buzzfeed were taking off. She scored roles on episodes of Crashing on HBO, The Marvelous Mrs. Maisel on Amazon, and Your Pretty Face Is Going To Hell on Adult Swim, and she began appearing in national TV commercials. That jumpstart gave her the juice to go Hollywood, where she co-hosts a live comedy showcase, “Everything’s Great,” with Nick Kocher and Demi Adejuyigbe every month at Dynasty Typewriter. In 2022, Addie plays a wiccan high-schooler in the Hulu romcom, Crush, and co-stars in the film, Mack & Rita, starring Diane Keaton. She sat down with me in Los Angeles to talk about her career, sharing her life on social media via Instagram Stories, hosting an impromptu election party in a gas station parking lot, martial arts and more.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Karen Chee is a writer and performer for Late Night with Seth Meyers. She has previously written for the Golden Globes and the Amazon Prime Video special, Yearly Departed, has developed TV pilots for Netflix and Comedy Central, and has published humor pieces in The New Yorker and McSweeney’s. All before the age of 27. No wonder she made Variety’s “Power of Young Hollywood” list as well as Forbes “30 Under 30.” Chee sat down with me to talk about getting an early start on her comedy career, how Twitter did or didn’t help her get her dream gig, and how she has managed supporting her grandparents in Korea during the pandemic while still writing remotely for Late Night, and picking up a new gig writing for Pachinko on Apple TV+.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Alison Leiby is a writer and comedian who started her own showcase at the Upright Citizens Brigade Theatre in New York City called It’s A Long Story. Leiby’s story is still being told. In TV, it has included late-night writing on staff for Comedy Central’s The President Show, and The Opposition with Jordan Klepper, as well as The Marvelous Mrs. Maisel. She’s written jokes for Triumph the Insult Comic Dog, published essays in McSweeney’s, Cosmo, Marie Claire and The New York Times. And her initial work punching up jokes for Broad City has led to a lengthy working relationship with Ilana Glazer. Leiby executive-produced Glazer's Comedy Time Capsule and her Amazon Prime Video stand-up special, The Planet is Burning. Glazer now is presenting Leiby in her first Off Broadway production of Alison Leiby: Oh God, A Show About Abortion, which begins previews April 25, 2022, at the Cherry Lane Theatre in Manhattan for a limited six-week run. Leiby sat with me to talk about how her comedy and writing career evolved from late-night TV to prestige comedy to her own very personal and politically active work.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Irene Tu is a Los Angeles-based stand-up comedian, actor, and writer. After moving to Berkeley from Chicago, she quickly established herself in the Bay Area comedy scene. The San Francisco Chronicle singled her out as an “artist on the brink of fame,” while other outlets have named her to the lists of “Bay Area’s 11 Best Stand Up Comedians,” “Women to Watch” and “Comedians You Should and Will Know in 2019.” She has performed on Comedy Central, LOGO, Starz, and Viceland, and has opened on the road for comedians such as Patton Oswalt, Maria Bamford, and most recently, Taylor Tomlinson. Tu released her debut album in March 2022 via Blonde Medicine — We’re Done Now is a hilarious 15-track collection of stories about coming out and dating, observations about food, dictators, and diva cups, as well as morbid musings about surviving the apocalypse. Proving she can put up with anything, she sat down with me outside in the cold for a quick chat about her album and her career.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Gilbert Gottfried invited me into his home in 2017 so he could remind us what kind of comedian he was before 2001, why he decided to launch into “The Aristocrats” at the Friars Club Roast of Hugh Hefner for Comedy Central, and how it completely changed the arc of his career. But first, listen to the version of the joke he recorded for his 2005 special, "Dirty Jokes."
This episode originally aired in 2017 as part of "On Second Thought," a series I did for Laughly, an app that no longer exists.
Toronto has a rich history of producing great sketch comedy performers and troupes that have crossed over in the United States. Among the TV series: SCTV. Bizzare. The Kids in the Hall. Baroness Von Sketch Show. And now the foursome from the sketch group, TallBoyz II Men, who broke out quickly from the 2018 Toronto Sketch Comedy Festival, premiering their own TV show on the CBC in 2019. TallBoyz — created by and starring Guled Abdi, Vance Banzo, Tim Blair and Franco Nguyen, and brought to TV by showrunner, director and Kid In the Hall Bruce McCulloch — not only won multiple Canadian Screen Awards in 2022. They also hosted the ceremony; and already celebrating as their show got picked up in the U.S. The first season of TallBoyz premiered on Fuse in March 2022, with seasons two and three to air later in the year. Guled and Franco sat down with me to talk about their rapid rise in the business and what it’s like to make sketch comedy with one of the greats.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Katie Hannigan taught preschoolers and performed as a mime before embarking on a full-time career as a stand-up comedian. So far, so good. Hannigan was a New Face at Just For Laughs Montreal, made her late-night TV debut on The Late Show with Stephen Colbert soon after. Hannigan has appeared on Comedy Central, MTV and The Travel Channel, developed a game show for the History Channel, and wrote a horror-comedy series for SnapChat. She currently co-hosts a podcast with comedian Sarah Tollemache, Lady Journey, and in March 2022, she released her debut comedy album, “Feeling of Emptiness.” Hannigan spoke with me about those past experiences, as well as studying in Russia, pretending she’s a garden statue, and how she’s the captain of her own ship steering her comedy career.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Matt McCarthy began his comedy career as the Fordham Ram mascot, but quickly carved out a spot for himself in New York City’s stand-up scene, scoring TV credits with Comedy Central on both Live at Gotham and John Oliver’s New York Stand Up Show. You may recognize him from his previous sketch comedy work on Conan, or from his many TV commercials, including a long-running stint as “the cable guy” one-upped by Verizon Fios, and more recently in national campaigns for Progressive and Planet Fitness. He’s also performed as recurring characters on both Adam Ruins Everything and Corporate. For a couple of years, McCarthy combined his comedy and wrestling fandom to write plot lines for the WWE. But it’s his personal and professional relationship with Pete Holmes that’s paid lasting dividends, from their early DIY videos that got them on TV during the Super Bowl, to a talk show on TBS, and they’re now reunited in 2022 on, How We Roll, the new CBS sitcom based on the real life of professional bowler Tom Smallwood. Matt joined me over Zoom to talk about his life and career, with plenty of funny stories about TV advertising, professional wrestling and carving out a separate niche for himself on TikTok as the ultimate film collector.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!
Ben Rosenfeld was born in the city formerly known as Leningrad, but came to Connecticut as a toddler with his parents as the Soviet Union began to break apart. His comedy reflects his upbringing as a Russian Jewish immigrant in America. A graduate of Rutgers University, Ben entered a Ph.D. program in neuroeconomics at CalTech before realizing that his career path was meant for comedy instead. His TV credits include Laughs on FOX, as well as The Nick Cannon Show, and he has released multiple comedy albums since 2012: “Neuro Comedy,” “The Russian Optimist,” “The United States of Russia” and “Don’t Shake Your Miracle.” Ben also has published an illustrated coffee table book, “Russian Optimism: Dark Nursery Rhymes To Cheer You Right Up.” That optimism seemed needed more in 2022 than even in 2016, ever since Russia invaded the Ukraine. Ben has tried to find jokes in that, too, producing daily TikTok videos to his more than 270,000 followers. He joined me over Zoom to talk about his comedy career, his Russian heritage, and how he has had to adapt to audiences as the geopolitics have changed.
If you like this conversation, please consider subscribing to my Substack called Piffany at Piffany.Substack.com so you can read bonus commentary on this episode as well as more comedy news and insights. Thanks in advance, and now that that’s out of the way, let’s get to it!