He is known for his dark comedy style, which emphasizes ironic misdirection, non sequiturs, biting insults, an arrogant demeanor, and a stage persona that frequently takes amoral stances.

Jeselnik was a writer for Late Night with Jimmy Fallon in its first season and hosted a Comedy Central Presents in 2009.

In 2013, he hosted his own Comedy Central series for two seasons, The Jeselnik Offensive, and released his second album, Caligula, which doubles as an hour-long stand-up special.

The second season debuted in 2018 on the Comedy Central Podcast Network under the slightly different name of The Jeselnik & Rosenthal Vanity Project (or JRVP).

On one occasion, a classmate was moving to a different town that was not generally regarded well, and Jeselnik cracked a sarcastic comment: "Oh, well, send us a postcard.

"[4] He would often stay up attempting to watch Saturday Night Live and, as he grew older, The Ben Stiller Show and Mr.

His original dream was to write the great American novel, but an internship in Los Angeles between his junior and senior years of college convinced him there were other avenues for a writer.

by Borders, he worked behind the scenes as an accounting clerk for the TV series Deadwood, during which time he would perform at open-mic nights.

[4] Inspired in part by Mitch Hedberg, Dennis Miller, Sarah Silverman,[8] and Steven Wright, it was two years into his stand-up comedy career when Jeselnik had a "lightbulb moment".

[9] Jeselnik's Comedy Central Presents stand-up special premiered in 2009, and he was named one of Comedy Central's breakout comedians of the year alongside Nick Kroll, Aziz Ansari, Whitney Cummings, Donald Glover, Matt Braunger, T. J. Miller, Kumail Nanjiani, and Jon Lajoie.

His dream job, predating stand-up or his first comedy class, was to sit around a table and "throw out jokes with people you respected.

[11] Jeselnik would work hard each day for the show and then proceed to go to Comedy Cellar, have a "big stiff drink", and do his act, feeling "miserable".

As such, the sketch opened the first episode and received a positive reception; Jay Leno called to inform Jeselnik "how much he loved the cancer segment.

[19] The hourlong special offers Jeselnik's trademark dark humor for the first forty minutes and personal anecdotes for the last twenty.

He discusses his grandmother's funeral, the Boston Marathon bombing, the cancelation of The Jeselnik Offensive, and the death threats he receives.