Canadaland is a Canadian podcast founded by Jesse Brown, who was a co-owner of Bitstrips, a company that makes avatars and had also worked as a media hoaxster and a humour columnist, before launching a career as a media critic.

The podcast began with a focus on media criticism and later transitioned to commentary on political issues and current affairs more broadly. Canadaland currently airs four days a week. It is hosted three days a week by Brown and once a week by Noor Azrieh.

At one time, the company produced other weekly or monthly podcasts covering a range of topics. As of 2024, only the flagship show, Canadaland, remained.

The podcast began in the fall of 2013 as a one-person project by businessperson Jesse Brown, focused on media criticism. By 2015, it had expanded into a small podcast network covering entertainment and some news.

In February 2014, Canadaland reported that CBC anchor Peter Mansbridge had been paid by the Canadian Association of Petroleum Producers (CAPP) to speak at a 2012 event, raising concerns about a conflict of interest given The National’s coverage of the oil sands. The story was picked up by The Huffington Post, Vice, sparked public debate, and prompted an investigation by CBC's Ombudsperson, who found that Mansbridge had not broken any rules but cautioned reporters about the optics of accepting money from groups likely to appear in the news. In April 2014, CBC tightened its rules on paid speaking engagements.

In May 2023, Brown decided to step back from the editor-in-chief role and Karyn Pugliese, a veteran journalist, was named the new editor-in-chief of Canadaland. An Algonquin journalist from Pikwàkanagàn, she is known for her leadership at APTN, CBC's investigative unit, and the Assembly of First Nations. A past president of the Canadian Association of Journalists, she is also a press freedom advocate. Pugliese had previously appeared on Short Cuts, and as the host of canadaLANDBACK.^{[citation needed]}

In October 2023, after the October 7 attacks, Brown intensified his social media activity, focusing on pro-Palestine protests and antisemitism in Canada. He also published statements on his X account and website criticizing female journalists who questioned the scale of Israel's retaliation against Palestinian civilians. This triggered the Canadaland Union to publish a letter on behalf of unionized and non-unionized employees, stating that Brown had “published a series of misleading and targeted statements through both personal and official channels” that undermined journalistic standards. The Union letter recognized that Brown's stated intentions were to bring attention to antisemitism but "The manner in which he's done this has been irresponsible." Brown faced additional backlash for his perceived stance on the Israeli-Palestinian conflict, estimating a 9% loss in Canadaland's supporters during this period.

In October 2024, Brown edited an interview on a show hosted by award-winning journalist Justin Ling, despite Ling's objections. The edits included the removal of a statement linking Canada's arms sales to Israel to Palestinian deaths, and cutting the word "genocide." While Ling and his guest called the edits political, Brown defended them as improvements. The dispute led to the resignation of the host, Pugliese as editor-in-chief, and several other staff. Brown later confirmed he insisted on final approval of all company content and reclaimed the editor-in-chief position for himself.