Big Jay Oakerson

Big Jay Oakerson, born Jason Michael Oakerson on December 7, 1977, in Philadelphia , Pennsylvania, is an American stand-up comedian, radio host, podcaster, and actor renowned for his laid-back delivery and explicit, irreverent humor.

Oakerson began performing stand-up in the late 1990s in Philadelphia , where he earned a reputation as a "comic's comic" among peers, before relocating to New York City in the early 2000s to pursue broader opportunities. His career, spanning over two decades, emphasizes constant touring across the United States and the release of multiple comedy albums and specials that highlight his signature style of observational and crowd-work-driven routines. Notable stand-up releases include Live at Webster Hall (2016) on Comedy Central , the full-length special Dog Belly (2023) available on YouTube , and the crowd work special Them/They (2025) also on YouTube .

In radio and podcasting, Oakerson co-hosts the daily SiriusXM show The Bonfire on Faction Talk (channel 103), airing weekdays from New York City with comedian Robert Kelly, where the duo engages in unfiltered discussions, comedy bits, and guest interviews. He also co-hosts the long-running podcast Legion of Skanks with Luis J. Gomez and Dave Smith through the GaS Digital Network, known for its raw, no-holds-barred conversations on comedy , culture, and personal anecdotes since 2012.

As an actor , Oakerson has made supporting appearances in films including Hustlers (2019) and Isn't It Romantic (2019), often drawing on his comedic background for ensemble roles. His work across these mediums has solidified his status as a prominent figure in contemporary American comedy , blending traditional stand-up with modern media platforms.

Jason Michael Oakerson, professionally known as Big Jay Oakerson, was born on December 7, 1977, in Philadelphia , Pennsylvania .

Oakerson spent his early childhood in West Philadelphia.

As a child, Oakerson was known as a class clown among his friends. Later, his family relocated to Blackwood, New Jersey, for high school.

Oakerson attended Robert E. Lamberton High School in West Philadelphia during his early high school years. In his senior year, he relocated with his mother and stepfather to the Blackwood section of Gloucester Township, New Jersey , where he completed his high school education at Triton Regional High School in Runnemede.

His initial exposure to stand-up comedy came through Philadelphia's local scenes during his late teenage years, rooted in the city's diverse cultural backdrop that influenced his early humor. At age 19, shortly after high school, Oakerson began performing at the Laff House, a predominantly Black comedy club on South Street in South Philadelphia . As a young white performer in this environment, he initially succeeded with rudimentary, crowd-pleasing material like "shitty Jerry Springer jokes" tailored to a young, Black, hip-hop-oriented audience, but soon faced significant challenges when his sets failed to connect for weeks and months afterward.

These experiences in diverse, demanding comedy spaces compelled Oakerson to adapt rapidly, crafting observational jokes about figures like P. Diddy and urban superhero scenarios to engage skeptical crowds, which helped forge his raw, unfiltered style. The contrast between his background and the club's audience dynamic tested his resilience, emphasizing quick-witted improvisation over polished routines and laying the groundwork for his future approach to crowd work and boundary-pushing humor.

Big Jay Oakerson began his professional stand-up career in Philadelphia in 1999, performing at open mics and local clubs such as the Laff House, a predominantly Black comedy venue where he honed his skills alongside emerging talents like Kevin Hart and Keith Robinson. Known early on as a "comic's comic," Oakerson earned respect from fellow performers for his raw, unfiltered material delivered in urban club circuits during the late 1990s and early 2000s.