Rick Glassman at SXSW 2024 Conference and Festivals on March 10, 2024 in Austin, Texas. (Photo by Samantha Burkardt/SXSW Conference & Festivals via Getty Images) Rick Glassman has built a strong following with his podcast, Take Your Shoes Off, where the stand-up comic sees interviewing celebrity guests as almost the perfect first date.
“There’s flirting involved. And flirting doesn’t have to have romantic interest. Flirting to me is similar to repartee – you nudge a little, you push a little and you let them do the same,” Glassman tells The Hollywood Reporter while bringing his solo show, Ricky’s on the Loose, to the Just For Laughs festival in Montreal.
He argues the best podcasts are where the vibe of two people meeting for the first time elicits light banter, jokes and playfulness and even subtle courting to see if his guests can work together on movies or TV series Glassman may have in the works.
Related Stories
THR Cover 'Ted Lasso' Was Finished. Then Jason Sudeikis Had an Epiphany
News Chris Fleming, Lisa Gilroy, Atsuko Okatsuka Among 2026 Just For Laughs Award Winners
His recent guest comedians, actors, directors and musicians include Alison Brie, Lisa Gilroy, Adam Ray making his 28th appearance, Nick Kroll and veteran showrunner Bill Lawrence. “Using play allows you to just be more present, and when you’re present, you’re not projecting what people are doing or why,” Glassman insisted.
Asked whether his first dates — sorry, podcast editions — should ideally end with a kiss of sorts gets Glassman to his stand-up act, where talk of dating etiquette and rules fill his comedic quiver. “When do you kiss? Do you ask? How do you ask? I remember I used to be scared of going on dates because, if I’m supposed to go in to kiss, what if I don’t want to yet? And what if they don’t want me to yet?” he ventures.
So Glassman has settled on a podcast, instead, for celebrity connections, with an eye to second dates. “I love when people come on for a second time” on the podcast, he adds. Especially if they want to get high for the occasion as, Glassman explains, “I had a good time with you the first time. Let’s see what it’s like when we’re extra silly.”
Of course, Glassman continues with movie and TV work, with recent credits including recurring roles on The Comedians and Nobodies. After an upcoming European swing for his comedy tour, Glassman will return for an undisclosed TV gig on the cards.
The Just For Laughs comedy festival wraps on the weekend.
THR Newsletters
Sign up for THR news straight to your inbox every day
Subscribe Sign Up
