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Deep Night Season 11: Emily Winter

Dale offers some helpful wedding planning advice to comedian and writer Emily Winter. Dale welcomes Emily for a conversation about producing live comedy events, turning failures into a positive force, getting over her fear of Park Slope doors, and working in Times Square. Emily shares her own path in comedy which included some prized internships,…

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Deep Night Season 11: Ann Carr

Dale makes direct and lasting eye contact with actor, writer, and director Ann Carr. Dale conjures up a conversation with Ann about her path from a farm-adjacent upbringing in Iowa to performing in sketch groups at UCB and landing memorable starring roles in film and television. Ann shares some thoughts on becoming a parent, acting…

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Deep Night Season 11: Live with Mallory O’Meara, Monroe Martin, and Todd Barry

Dale breaks the surface of his personal black lagoon to present this special monster-movie inspired episode of the program, featuring Dale and his guests Todd Barry, Monroe Martin, and author Mallory O’Meara. Recorded live at The Slipper Room, the show begins with Dale spreading the word about the growing threat of sewer monsters beneath New…

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Deep Night Season 11: Aminah Imani

Dale absorbs some sound advice from comedian and new best friend, Aminah Imani. Dale and Aminah talk about the practical side of living as a comedian in New York, which includes how to thrive by staying within your means. Aminah brings her Frugal Fridays knowledge to the Deep Night, as the two talk layaway plans…

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Deep Night Season 11: Jenny Gorelick

Dale marvels at the relentless energy and inventiveness of comedian, actor, and producer, Jenny Gorelick. It turns out that Jenny and Dale have a lot in common, from loving birthday celebrations to attending the same prestigious theater program at Brown University. Reflecting back on his time in Providence, Dale recalls his younger self, full of…

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Deep Night Season 11: Shaina Feinberg

Dale vision wheels his way through some serious seasonal feelings in this episode with filmmaker and writer, Shaina Feinberg. Dale and Shaina have both grappled with the passing of a parent and while Shaina has used her grief to generate important new works of cinema, Dale has spent several hours not doing anything in front…

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Deep Night Season 11: Remy Kassimir

Dale blushes through his turtleneck in this special, all-sex Valentine’s Day episode of the program. Dale welcomes comedian Remy Kassimir to the show to talk about her life and work, and how the two intersect in her podcast, How Cum. Remy went on a very personal journey of discovery on her show, learning how to…

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