#1007 - Ari Shaffir, Bert Kreischer & Tom Segura

Ari Shaffir (born February 12, 1974) is an American stand-up comedian, podcaster, actor, writer, and producer recognized for his provocative humor that frequently examines taboo subjects, personal vices, and societal hypocrisies through a skeptical lens. After growing up in an Orthodox Jewish family and studying at a yeshiva in Israel, Shaffir graduated from the University of Maryland with a degree in English and moved to Los Angeles to launch his comedy career, initially working as a doorman at The Comedy Store. He gained prominence through stand-up specials such as Passive Aggressive (2013), Double Negative (2017), Jew (2022), and America's Sweetheart (2024), alongside hosting the storytelling series This Is Not Happening on Comedy Central. From 2011 to 2023, Shaffir produced and hosted Ari Shaffir's Skeptic Tank , a podcast featuring interviews with experts and individuals to probe human motivations, pseudoscience, and experiential narratives. Shaffir's unapologetic approach has sparked controversies, including a 2020 video on social media deriding the death of Kobe Bryant, which prompted backlash from celebrities and fans but was upheld by Shaffir as emblematic of his boundary-pushing style unbound by public mourning rituals. Ari Shaffir was born in New York City to parents of Romanian Jewish descent, with his father, Nat Shaffir (born Nathan Spitzer in 1936), a Holocaust survivor who lost 32 family members and emigrated to Israel before settling in the United States in 1961. The family initially adhered to Conservative Jewish practices during his infancy and early years in Greensboro, North Carolina . At around age nine, the Shaffirs relocated to Silver Spring, Maryland , where they adopted Orthodox Jewish observance, transitioning from a more lenient approach to stricter adherence to halakha (Jewish law). This move immersed Shaffir in a Modern Orthodox environment, characterized by daily Torah study , Shabbat observance, and communal isolation from non-religious influences to preserve piety. The Orthodox framework emphasized ritual discipline and ethical rigor, fostering a worldview centered on divine covenant and moral absolutism , though it also highlighted tensions with broader American secular culture evident in Maryland's diverse suburbs. Shaffir grew up in an Orthodox Jewish family in Kemp Mill, Maryland, part of Montgomery County, after earlier relocations from New York City and Greensboro, North Carolina . He attended Jewish day schools and Hebrew academy during his formative years, immersing him in religious observance and community traditions. He completed high school in nearby Rockville, where exposure to broader social dynamics began introducing tensions between his insulated upbringing and external influences. Following high school, Shaffir studied briefly at Yeshiva University , adhering to strict religious study, before transferring during his sophomore year to the University of Maryland, College Park . There, he earned a bachelor's degree in English literature in 1999, shifting focus to arts courses including screenwriting . This transition marked a pivotal departure from religious orthodoxy, as the secular campus environment—characterized by diverse ideologies and personal experimentation, such as marijuana use—clashed sharply with his prior god-fearing lifestyle, prompting initial doubts about inherited doctrines. At the university, Shaffir engaged with prevailing campus subcultures, including leftist-leaning activism and intellectual debates, but these encounters fueled rather than reinforced dogmatic adherence. Assigned initially to political science coursework, he observed ideological rigidities akin to those in his religious background, leading him to question unchallenged assumptions across spectrums.

Albert Charles Kreischer Jr. (born November 3, 1972) is an American stand-up comedian, actor, podcaster, and television host. Kreischer rose to prominence in 1997 when Rolling Stone magazine profiled him as the top partier at Florida State University, a designation that highlighted his fraternity involvement and delayed graduation due to excessive socializing. This exposure led to early television appearances and a pivot to professional comedy, where he developed a style characterized by animated storytelling, physical comedy, and autobiographical material drawn from his personal life. His notable works include hosting the Travel Channel series Bert the Conqueror from 2010 to 2014, multiple stand-up specials on platforms such as Netflix ( The Machine , Secret Time , Hey Big Boy , Razzle Dazzle , and Lucky ), and starring in the 2023 action-comedy film The Machine , which he also produced based on a real-life anecdote from his college years involving Russian gangsters. Kreischer hosts the long-running podcast Bertcast , featuring interviews with comedians and celebrities, and co-hosts 2 Bears, 1 Cave with Tom Segura , both under his production company Berty Boy Productions, which he founded in 2022. In 2022, his live tour ranked fourth on Pollstar's list of highest-grossing comedy tours, reflecting his commercial success in the industry. Albert Charles Kreischer Jr. was born on November 3, 1972, in St. Petersburg, Florida, and raised in Tampa alongside two younger sisters, Annie and Kottie. His father, Albert "Al" Kreischer Sr., worked as a real estate attorney and had aspired for Bert to pursue baseball at Duke University, while his mother, Margaret "Gege" Kreischer, was employed in an early childhood development organization. Kreischer's parents provided a supportive environment that accommodated his outgoing and anxious personality, even as it manifested in extended partying during his later education ; Gege emphasized his happiness over conventional paths, and Al eventually endorsed his unconventional career trajectory despite initial reservations. Specific anecdotes from Kreischer's accounts highlight a family dynamic tolerant of his energetic tendencies from childhood, though detailed public records on early family life remain limited beyond his self-reported stories in podcasts and interviews. Kreischer enrolled at Florida State University (FSU) in the early 1990s, majoring in English with a focus on creative writing , and became a member of the Alpha Tau Omega fraternity. He earned a reputation for heavy partying amid FSU's status as a prominent party school , often prioritizing social activities over academics; by 1997, he was in his sixth year as an undergraduate, admitting in interviews to never having read a full book during his studies. During a 1995 summer study abroad program in Russia , Kreischer recounted becoming heavily intoxicated, befriending members of the Russian mafia , and participating in the robbery of a vodka train—an incident he later dramatized in his comedy routine "The Machine." In April 1997, Rolling Stone magazine profiled Kreischer in a six-page feature titled "Bert Kreischer: The Undergraduate," dubbing him the "top partier at the Number One Party School in the country" after ranking FSU highest in their party school survey. The article detailed his exploits, including frequent all-night drinking sessions and minimal academic engagement, which Kreischer later credited with launching his public persona despite straining relations with FSU faculty; he alleged a spiteful English professor withheld final approval for graduation over the piece's portrayal of the department. Kreischer participated in FSU's 1997 commencement ceremony but faced delays in receiving his degree, ultimately listed as a 1997 Bachelor of Arts recipient by the university's English department, though some FSU announcements reference 1998 completion after resolving requirements.

Thomas Weston Segura (born April 16, 1979) is an American stand-up comedian, actor , writer, podcaster, and author known for his dark humor and observational comedy style. Born in Cincinnati , Ohio , Segura began performing stand-up in the early 2000s and has risen to prominence as one of the top touring comedians worldwide, with sold-out arenas and international tours such as his "I'm Coming Everywhere World Tour" featuring over 300 shows. He has released six Netflix stand-up specials: Completely Normal (2014), Mostly Stories (2016), Disgraceful (2018), Ball Hog (2020), Sledgehammer (2023), and Teacher (2025). In addition to stand-up, Segura has built a successful career in podcasting, co-hosting Your Mom's House with his wife, comedian Christina Pazsitzky , since 2010, which has become one of the most popular comedy podcasts available on platforms like Spotify and Apple Podcasts . He also hosts 2 Bears, 1 Cave alongside fellow comedian Bert Kreischer , focusing on comedy, stories, and guest interviews. As an author, Segura published the New York Times bestseller I'd Like to Play Alone, Please in 2022, a collection of humorous essays drawn from his personal experiences. Segura's acting credits include notable roles in films such as Instant Family (2018), where he played Russ, a supportive friend in a family adoption story, and Countdown (2019), portraying Derek in the supernatural thriller. He has also appeared in television series like Gary Unmarried (2008–2010) and Happy Endings (2011–2013), and more recently created and starred in the Netflix sketch comedy series Bad Thoughts (2025), a dark humor anthology that premiered on May 13, 2025. Married to Christina Pazsitzky since November 8, 2008, the couple has two sons, Ellis (born 2016) and Julian (born 2018), and resides in Austin, Texas . Thomas Weston Segura was born on April 16, 1979, in Cincinnati , Ohio , to Thomas Nadeau Segura and Rosario "Charo" Lazarte. He has two older sisters, Maria and Jane. His father, an American of Spanish, Cajun, and French-Canadian descent, served as First Vice President at Merrill Lynch after the family relocated from Peru following his marriage to Lazarte in Lima in 1976. His mother, a Peruvian immigrant, brought elements of her South American heritage into the household, including a background rooted in Lima where the couple met. Segura grew up bilingual in Spanish and English, primarily due to his mother's limited proficiency in English, which led her to communicate with him and his siblings in Spanish from a young age. This linguistic environment, combined with annual summers spent in Lima , Peru , deeply influenced his cultural identity, fostering a strong connection to his Peruvian roots amid his American upbringing. The family frequently relocated due to his father's career, spending Segura's early childhood briefly in Cincinnati before moving to Minneapolis , Minnesota , and later settling in Vero Beach, Florida , where he completed high school. He graduated from Saint Edward's School in Vero Beach in 1997. Segura's early exposure to humor stemmed from family dynamics, particularly his mother's role as a natural comedic storyteller, and the unique challenges of immigrant experiences, such as navigating cultural differences and language barriers in everyday life. These elements provided formative influences that later informed his comedic perspective on heritage and identity. Segura attended Lenoir-Rhyne University in Hickory, North Carolina , where he earned a bachelor's degree . His time there represented a pivotal period in his development, bridging academic life with emerging creative interests. During his freshman year, at age 18, Segura overdosed on the drug GHB, was clinically dead for three minutes, and spent time in a coma before recovering. During his college years, Segura made his initial foray into stand-up comedy , participating in open mic events on campus that allowed him to test early material.