He chronicles his drinking and sexual encounters in the form of short stories on his website TuckerMax.com, which has received millions of visitors since Max launched it as the result of a bet in 2000.

[25][26] In 2006, he began development of a television pilot for Comedy Central, but the project was canceled reportedly due to a dispute with Sony about feature film rights.

He reportedly received a $300,000 advance for Assholes Finish First, and released a revised and expanded edition of I Hope They Serve Beer in Hell in January 2009.

[37] In February 2012 a publicity campaign for his book Hilarity Ensues led to his account with the company Sponsored Tweets being banned for "ethics violations".

[39] In September 2015, Max and Dr. Miller released Mate: Become the Man Women Want, an advice book about men's sexual strategies published by Little, Brown and Company.

[40] In November 2014, Max published his experience of working with Melissa Gonzalez, CEO of the Lionesque Group for her book The Pop-Up Paradigm – the first project of his company Scribe Media.

[46] In 2017, Max ghostwrote Tiffany Haddish's memoir, The Last Black Unicorn, which was released in December 2017 by Simon & Schuster and debuted at number 15 on The New York Times best-seller list.

[48] The term, combining "fraternity" and "satire," was introduced by The New York Times reporter Warren St. John in a 2006 article titled Dude, Here's My Book.

In January 2006, Max posted a thread on his message board satirizing Anthony DiMeo, a young Philadelphia socialite, for throwing a New Year's Eve party that was a disaster.

[55][56] The lawsuit was subsequently dismissed under the Communications Decency Act, with U.S. District Judge Stewart Dalzell noting that although Max could be a "poster child for vulgarity", the law must protect "the coarse conversation that, it appears, never ends on TuckerMax.com.

"[57][58][59] In May 2009, Max held a speaking engagement which was picketed by a feminist group at Ohio State University, who claimed that his writing "promoted a culture of rape.

"[60] In August 2009, the North Carolina State University Women's Center held a silent protest of I Hope They Serve Beer in Hell.

[65][66] In 2012, hoping to offset a part of his owed taxes in a way that also provided self-promotion, Max reportedly offered to donate $500,000 to Planned Parenthood if they named an abortion clinic after him.