Barstool began in 2003 as a weekly print publication distributed for free at transit stops in the Boston metropolitan area that offered gambling advertisements and fantasy sports projections but later expanded to encompass other topics.

[1] In August 2011, the site received criticism over nude photos of American football quarterback Tom Brady's two-year-old son, which was accompanied by comments describing the size of the child's genitalia, which a former prosecutor suggested was sexualization of a minor.

"[4] Other elements that have received criticism include comments such as "we don't condone rape of any kind at our Blackout Parties ... however if a chick passes out that's a gray area".

[5] Portnoy, in response, has stated that, "...It's not our intent, with jokes, to poke fun at rape victims," while pointing out the satirical nature of the site's content.

[6] A Northeastern University protest group called Knockout Barstool held a demonstration outside of a 2012 Blackout party at Boston's House of Blues.

[1] In 2011 and 2012, the BarstoolU brand ran the "Barstool Blackout Tour", a series of electronic dance parties with as many as 2,500 attendees at venues in cities and college towns on the East Coast and in the Midwest.

[12] On January 7, 2016, private equity firm The Chernin Group (TCG) purchased a 51% majority stake in Barstool Sports, valuing the company at between $10 and $15 million.

After an initial phone call, Kerns flew to Boston to have dinner with Portnoy, discuss the Barstool vision, and begin preliminary investment talks.

[17] The show made headlines on February 2, 2017, after Indianapolis Colts punter Pat McAfee announced during a segment of that night's episode that he was retiring from the NFL to become a contributor to the site.

[21] The show's removal came after past statements from Barstool president Dave Portnoy resurfaced, one of which involved calling current ESPN employee Sam Ponder a "slut".

[26] On March 28, 2018, NBA player Frank Kaminsky launched a Barstool podcast, Pros and Joes, hosted by himself and three high-school friends.

Penn National announced that they would be matching all first-time deposits by donating to the Barstool Fund, raising a total of $4,550,280 for Michigan small businesses.

[28] On August 8, 2023, David Portnoy announced that Penn Entertainment had ended its relationship with Barstool Sports and had divested ownership of the company back to him.

The agreement stipulates that Penn will receive 50% of the gross proceeds of any future sale of Barstool, but Portnoy stated that he planned to maintain his ownership of the site "till I die".

This deal kicked off with a live-streamed free-throw challenge event featuring Barstool talent, where viewers could win part of a $100,000 prize pool.

[41] Barstool was described as the "Bible of Bro Culture" and a must-read for the "dude zeitgeist" for its committed audience of young men, primarily in the 18–35 age demographic, who felt disenfranchised by the mainstream media.

[42] The site contains a mixture of podcasts, blogs, and video series featuring company staff in what has been described as "a sort of online reality show: Every office argument and personal-life development was written up and fed to a growing legion of 'Stoolies'.

After Bredouw eventually refused to rescind her complaint in exchange for $2,000, Barstool filed a counter-claim asking Twitter to reinstate the video, alleging that the take-down was an error.

[47] Barstool owns Old Row, a sports blog it bought in 2016, and the company also operates Rough and Rowdy, and amateur proxy contest.

Both Barstool and Chicks pages repost campus submissions, such as ones where students are encouraged to submit screenshots of chats from dating apps.

Even though it was later taken down, USC student Sasha Ryu criticized both the account and the anonymous people who submitted the footage as being responsible for creating a culture of everybody recording everything.

[51] Additional criticism of Barstool's Instagram accounts include an Arizona State University magazine citing the account for causing more damage than community connnection,[52] from Ithaca College's newspaper for inciting a toxic sports fanbase,[53] and Marquette University's student newspaper for refusing to take down content even when students request so.

[62] Barstool also produces numerous podcasts, including programming from David Portnoy, Spittin' Chiclets, Pardon My Take, The Kirk Minihane Show, Chicks in the Office as well as podcasts from Barstool bloggers and professional athletes and celebrities such as Deion Sanders, Alex Rodriguez, Josh Richards, Ryan Whitney, Paul Bissonnette, Colby Armstrong, Patrick Beverley, Jake Arrieta, Arian Foster, Paddy Pimblett, Molly McCann, Jim Florentine, Jamie Dukes, Taylor Lewan, Will Compton, and Mark Titus.