Oakley began making videos in 2007; his first video Raindrops had received almost 500,000 views on YouTube as of January 12, 2020. Since uploading his first video in 2007 while a freshman at Michigan State University, his channel has over 682 million views, and, at his peak, over 7. 3 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 January 2020[update] he also had more than 6 million followers on Twitter and 5. 9 million on Instagram.
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