"What the Buck?" began as a small weekly segment on Table for Two and gave him "a chance to riff and rant on his own." His cousin then posted some on YouTube and "it snowballed." Buckley started building a following on MySpace and started his YouTube channel in May 2006, with his main focus centered on celebrities and pop culture, often satirizing and parodying them. On September 11, 2008, he quit his low-paying day job as an administrative assistant for Live Nation, a music promotion company and began earning more money as an online entertainer. Edge Boston summarized his work as: "Three or four times a week, he uploads his slickly made commentaries on celebrities and pop culture that are amongst the snarkiest to be found on the web." His high-energy and rapid-fire delivery and style has been described as being "irreverent, fast-talking, pop-culture-obsessed"; he has been likened to "a living can of Red Bull." He is one of the most subscribed vloggers rising to be the second most popular comedian within the first five months of posting. His online success has led to more mainstream media work including DirectTV, Leeza Gibbons's syndicated radio show, a regular guest spot on Fox News Channel's weekly gossip show Lips & Ears and Red Eye.

On September 6, 2007, "The Top (& Bottom) Gays of YouTube!", the first all-gay collaboration video by YouTube's most subscribed video bloggers, was posted by Buckley to create a "YouTube gay village." Featuring James Majesty, Chris Crocker, William Sledd, and "Gay God" (Matthew Lush), the video consisted of each of the four bloggers commenting on the others' vlogging, with Buckley acting as host for the various outtakes. As of July 2013 in the rankings of most subscribed channels, in all categories, "What The Buck?" is 428th. As of November 2008, the video has been viewed over 1,000,000 times, with over 8,500 comments. On April 23, 2008, Buckley began to broadcast regular live shows on the social broadcasting website, BlogTV. His live shows have already been viewed by over 200,000 people. He moved from BlogTV to YouNow and appeared Tuesday nights at 5pm Eastern, but has stopped YouNow broadcasting and switched to ConnecTV, a site where users can text chat about TV shows live.

He has started a YouTube channel titled BuckNews, a spinoff of What the Buck? in which he included content that did not make his main show. Additionally, Buckley has introduced two spin-off shows: Pass the Buck and Buck Factor which promoted the interaction between him and his fans, but no longer produces these. He has since closed his account "BuckNews".

In December, Buckley was part of the BBC's Most Annoying People as an interviewee.

In March 2010, Buckley was nominated for a Streamy award in the category of "Best Web Series Host". Additionally Michael has created a new show titled "Dear Buck" where he answers questions posted on his website, Twitter, Facebook, and/or previous Dear Buck shows.

He currently has over 1 million subscribers.

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