Barstool first launched as a print publication in 2003, which was distributed in the Boston metropolitan area offering gambling advertisements and fantasy sports projections, but later expanded to encompass other topics. It launched on the Internet in 2007. In April 2014, AOL announced that they would be airing exclusive online content from Barstool Sports.
Chernin Group president of digital Mike Kerns appeared on the inaugural episode of Portnoy's podcast, The Dave Portnoy Show, to discuss the acquisition. During the appearance, Kerns and Portnoy detailed the beginning of their talks, when Kerns was put into contact with Portnoy via a mutual friend and former University of Kentucky quarterback Jared Lorenzen. After an initial phone call, Kerns took a private plane from San Francisco to Boston in order to have dinner with Portnoy, discuss vision for Barstool and the future of the brand, and begin preliminary talks of an acquisition.
Following the acquisition, and as a result of no longer being the majority owner, Portnoy adopted the title of Chief of Content. Barstool U head writer Keith Markovich, a.k.a. KMarko, was also announced as the sites' new head editor. On July 19, 2016, Erika Nardini, former chief marketing officer of AOL, was announced as the CEO of Barstool Sports.
During the week of Super Bowl LI, Barstool broadcast a televised version of The Barstool Rundown live from Houston on Comedy Central. 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. On June 19, 2017, the site announced that Michael Rapaport would be joining Barstool Sports and hosting a podcast.
Barstool Van Talk
On October 18, "Barstool Van Talk" debuted on ESPN2. The show starred Pardon My Take personalities PFT Commenter and Dan "Big Cat" Katz. It was cancelled after one episode, with ESPN Inc. president John Skipper citing concerns about distinguishing the content of Barstool from that of ESPN. The show's removal came in the wake of complaints from staff at the network, most notably Samantha Ponder.
Following a round of fundraising reported in January, Barstool is said to have received a valuation of $100 million. According to CEO Erika Nardini, The Chernin Group has invested $25 million in the website. On February 18, Michael Rapaport was fired after making a derogatory comment towards the site's fan-base.
In April 2017, listeners of the Barstool Podcast, Pardon My Take, raised over $50,000 for the Justin J. Watt Foundation.
David Portnoy has described the site's topics as "sports/smut." 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'." Barstool also owns and promotes Rough N’ Rowdy, an amateur boxing league which the company showcases through pay-per-view events.
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. Portnoy argued that the comments were meant to be humorous in tone and were not intended to be seen as sexual.
The site has received repeated criticism over content posted on Barstool Sports that critics of the site allege normalizes rape culture. Comments that have sparked debate include a post on a 2010 blog where Portnoy said "[E]ven though I never condone rape if you're a size 6 and you're wearing skinny jeans you kind of deserve to be raped right?" 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". 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. A Northeastern University protest group called Knockout Barstool held a demonstration outside of a 2012 Blackout party at Boston's House of Blues. Portnoy has been openly dismissive of the protest group and has accused them of being serial protesters.
The Blackout Tour parties were criticized for promoting excessive drinking and allowing underage drinking, as well as for assaults that have occurred at the proceedings. On February 2012, then–Boston mayor Thomas M. Menino expressed concern through a spokesperson over the parties' promotion of "excessive drinking to the point of blacking out" and that such promotion would not be a good message for the city. Massachusetts Alcoholic Beverage Control Commission agents and club security at a House of Blues event in Boston the following month confiscated 300 fake identifications and refused admission for around three-fourths of the event's 2000 ticket holders. Shortly thereafter Portnoy announced that the company would not be scheduling more of the events in Boston, stating that "it just doesn’t seem like Boston is friendly to nightlife of our sort, at least”.
In March 2019, Barstool was accused by comedian Miel Bredouw of having re-posted one of her videos to the site's Twitter account without attribution. 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. Following the dispute, data from Social Blade revealed that on March 6, 2019 Barstool deleted over 60,000 posts from its Twitter account and 1,000 posts from its Instagram account.