Oakley began making videos in 2007; his first video Raindrops has received almost 500,000 views on YouTube as of November 19, 2017. Since uploading his first video in 2007 while a freshman at Michigan State University, his channel has over 650 million views and, at his peak over 7.7 million subscribers. Oakley, who is openly gay, is a former member of the successful collaboration channel "5AwesomeGays," where he produced the Friday video for over three years. He was featured in the 2014 Frontline investigative report, "Generation Like," a follow-up on how teenagers are "directly interacting with pop culture" to the 2001 report, "The Merchants of Cool." SocialBlade, a website that rates YouTube and Instagram accounts, ranks his YouTube channel, as of November 19, 2017, with a grade "B", subscriber rank of 224th, video view rank at 2,010th, and a SocialBlade rating of 33,897th. As of September 2018[update] he also has more than 6.3 million followers on Twitter and 6.2 million on Instagram.\n', '

As of March 2013, Oakley co-hosted a weekly pop-culture news update – "Top That!" – with Becca Frucht for PopSugar until October 31 when he announced his departure. From 2013–14, he performed the voice of Mr. McNeely in five episodes of the comedy web series The Most Popular Girls in School. He has hundreds of thousands of followers on Facebook and Tumblr. In 2015, he released his first collection of humorous personal essays under the title Binge, via publishers Simon & Schuster.\n', '

Oakley was the host of The Tyler Oakley Show. The show aired weekly on Ellen DeGeneres’ ellentube platform. He was named one of Forbes\' 2017 30 under 30.\n', '

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