On March 10, 2008, Dawson made his YouTube channel, called “ShaneDawsonTV”. The earliest video that remains on the channel, “Kermit the Frog and Me,” was uploaded about four months later. When he first began making videos, he worked at Jenny Craig along with his mother and brother, but was fired in August 2008 after he uploaded a video of himself pole dancing in the building he worked at and showing before-and-after photos of clients, saying that “all these people gain their weight back.”

The video also included clips of his co-workers reading inappropriate passages of a book by Jenny Craig spokesperson Valerie Bertinelli. His mother, brother, and about six other coworkers who appeared in the video were also fired after the company saw it. In September, he uploaded a video called “Fred is Dead!”, which has since received over 25 million views.

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, the jock’s insecure girlfriend, a “fashionably bulimic” high school girl, “Aunt Hilda,” gothic girls, trans characters, and “Guadalupe”/”Fruit Lupe” (a Mexican with stereotyped chola accent).

Dawson would also portray either fictional or exaggerated versions of his own “relatives” and family members. One video sees Dawson pretending to be a high school student and feigning “illness” to avoid attending school for a day. The same video sees him wearing a bright-red wig, red lipstick, and matching red bathrobe to portray his “mother,” an alcoholic, “Southern,” lazy, and semi-abusive character. Despite Dawson’s own bisexuality and homosexual marriage, some instances of gay slurs in these skits drew criticism; his actual mother bears no comparison to this character. He also drew criticism for portraying a pre-op transgender female character, whose appearances included lines such as “I’m sick of this penis! Chop it off!” and explaining “and that’s how they’re going to turn my penis into a clitoris.”

Dawson occasionally posts new videos on his channel “ShaneDawsonTV” (mainly short web films, music video parodies, film trailer parodies, and original music) and formerly posted on his second channel “ShaneDawsonTV2,” now called “Human Emoji”; however, this channel has mostly been discontinued since 2012. His third and main YouTube channel, Shane, is where he previously posted vlogs and now posts original content Mondays through Fridays. He began using this channel in May 2010.

In November 2009, Dawson was featured on Attack of the Show!. In 2010, Forbes magazine named him their 25th most famous web celebrity.