[5] Dawson was one of the first people to rise to fame on YouTube after he began making videos in 2008 at the age of 19 and garnered over 500 million views during the next two years.

[6][7] Most of Dawson's early work consisted of comedy sketches in which he would play original characters, impersonate celebrities, and make light of popular culture.

In 2014, he directed, produced, edited, and starred in the romantic comedy film Not Cool and appeared on the accompanying docu-series The Chair.

From 2019 to 2020, he created and appeared in the docu-series The Beautiful World of Jeffree Star, which garnered over 130 million views.

[20] Dawson has released two New York Times best-selling books, I Hate Myselfie (2015) and It Gets Worse (2016), and his three YouTube channels have collectively accumulated over 4.5 billion views.

[27] In June 2020, YouTube indefinitely suspended monetization on all three of his channels and his books were pulled from shelves following a public backlash over numerous controversial comments he had made in the past, particularly regarding underage girls and zoophilia.

"[35] The video also included clips of his co-workers reading inappropriate passages of a book by Jenny Craig spokesperson Valerie Bertinelli.

[37] During this time, Shane performed as a number of "drug-addled, often drunk, cultural stereotype characters" in his skits, including: "ghetto girl" Shanaynay, "Ned the Nerd", gangster "S-Deezy", "Barb the Lesbian", a football jock/bully (who is a closeted homosexual), the jock's insecure girlfriend (who thinks she is overweight), a "fashionably bulimic" high school girl (whose finger is her "best friend" to aid in self-induced vomiting), "Aunt Hilda" (portrayed with a thick "New York-Jewish" accent), gothic girls, "trans" characters, and "Guadalupe"/"Fruit Lupe" (a Mexican with stereotyped chola accent).

[38] Dawson would also, in skits where he was playing himself, portray either fictional or exaggerated versions of his own "relatives" and family members.

Despite Dawson's own bisexuality and homosexual marriage, these instances of gay slurs drew some criticism at the time; his actual mother (who later appears in several videos) bears no comparison to this character.

Previously, the funding he needed for the pilot was provided by digital media group Take180 after he helped them out with acting in their own videos.

The song was released on March 31, 2012, on iTunes, with an accompanying music video debuting on his YouTube channel on the same day.

[49] On October 18, 2013, Dawson released a song entitled "Wanna Make Love To You", with Liam Horne.

On November 12, 2013, Dawson announced that he was developing the weight loss center project with Sony Pictures Television for NBC.

Darlene Hunt, Will Gluck, Richie Schwartz, Lauren Schnipper, and Dawson would serve as executive producers for the project.

[54][non-primary source needed] It was part of a Starz original series called The Chair, in which two novice directors are given the same script and must each make their own film from it.

[56] In December 2014, Dawson released a parody of Taylor Swift's song "Blank Space" on YouTube.

This video was found to be in poor taste by her labels, Big Machine Records and Sony, who removed it,[57] citing "copyright infringement".

[64] In August 2018, Shane continued the documentary format and covered makeup artist Jeffree Star in a five-part series titled The Secret World of Jeffree Star and also received high amounts of media attention[65] In September 2018, Shane covered YouTuber Jake Paul in an eight-part series titled The Mind of Jake Paul.

The series follows Dawson's investigation on the lifestyle of Paul, including research with licensed therapist Katie Morton on antisocial personality disorder.

[67] The second part featured Dawson investigating further topics, exploring the wider message "don't believe everything you see", including Adobe Voco voice manipulation, and Chuck E. Cheese pizzas.

[76] Having previously lived in Calabasas, California, he moved in August 2021 to Colorado, where he and Adams purchased a farm for $2.2 million.

[80] In July of the same year, they announced via Adams's vlog channel that they were expecting twin babies via surrogacy.

[83] Dawson has been criticized for his racial comedy, particularly his use of blackface in several skits impersonating Wendy Williams and Chris Brown, his use of the words "nigga" and "nigger" in multiple videos, and his jokes about "ghetto pranks" at the 2012 VidCon.

[84][85][86] In 2018, Dawson was the subject of a controversy regarding comments he had made about pedophilia on a 2013 episode of his podcast Shane and Friends, after which he published an apology video likening his comedic style at the time to that of shock jocks.

[88] He also claimed that he dealt with the pain from his childhood by making inappropriate jokes: "It is something I did for shock value or because I thought it was funny.

[89][90] On June 29, 2020, Target announced that it was "in the process of removing" Dawson's two published books I Hate Myselfie and It Gets Worse from its shelves.