Oakley began making videos in 2007; his first video Raindrops had received 523,392 views on YouTube As of February 1, 2021[update]. Since uploading his first video in 2007 while a freshman at Michigan State University, his channel has over 683 million views, and, at his peak, over 8 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 February 1, 2021[update], with a grade "B", subscriber rank of 1,434th, video view rank at 7,022nd, and a SocialBlade rating of 345,254th. As of February 1, 2021[update] he also had more than 5. 6 million followers on Twitter and 5. 6 million on Instagram.
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