Sassy Gay Friend is a YouTube web series created in 2010 by the online team of the Chicago-based improv company The Second City. The series starred actor Brian Gallivan as the titular character who visits famous characters from literature and film, as well as a handful of historical figures, to give them advice from the perspective of a over-the-top stereotypical homosexual male.
Brian Gallivan created the Sassy Gay Friend character in 2004 while performing in The Second City's mainstage show Red Scare. The first Sassy Gay Friend YouTube video was uploaded on February 17th, 2010 to the Second City's channel, depicting the character visiting Ophelia from William Shakespeare's Hamlet right before she commits suicide. He talks her out of drowning herself by reminding her Hamlet has a terrible attitude and stabbed her father. As of July 2013, the video has more than 6.4 million views.
The day after it was uploaded, the video was reshared on MetaCafe, followed by eBaum's World four days later. On February 23rd, it was reposted on Buzzfeed and Queerty. After the second episode (shown below) featuring William Shakespeare's Juliet was uploaded on March 8th, the series was featured on Flavorwire and Boston Edge. In April, Salon questioned whether the series was satire or reinforcing the cliche that all gay men are flamboyant. Throughout the rest of 2010, Sassy Gay Friend videos appeared on Paste Magazine, the Huffington Post, Entertainment Weekly, the New York Post and Trendhunter.
In February 2011, Sassy Gay Friend became the spokesperson for MiO, a liquid water enhancer product, doing a handful of man on the street interview videos (shown below) for the brand. That year, Sassy Gay Friend videos were featured on Time NewsFeed, Urlesque and Refinery29. Additionally, a Memegenerator page was created for advice animal style image macros using a picture of Gallivan on a pink background using catchphrases from the series. As of July 2013, it has gained more than 1,900 submissions.
 Flavorwire – 10 Literary Ladies in Desperate Need of a Gay Friend
 Entertainment Weekly – Clip du jour: Sassy Gay Friend saves the Giving Tree
 Time NewsFeed – Watch: What Your Sassy Gay Friend Is Really Thinking