“Othello,” “Romeo and Juliet,” “Hamlet” - these are some of the canonic works that students are required to read at some time throughout their school careers. Interestingly enough, all the female leads in those plays die because of their ill-fated connections with the central male figures. Which begs the question: What if they had had a sassy gay friend?

With this tongue-in-cheek inspiration, Brian Gallivan, aka “the Sassy Gay Friend,” created a YouTube series based first on the tragic female characters in Shakespeare’s works, and now on a variety of other pieces of literature, including the Bible and The Giving Tree.

His show rests on a combination of gay stereotypes and witty wink-wink-nudge-nudge “You have to know the story” dialogue that includes such soundbites as “There is something rotten in Denmark, and it’s his piss-poor attitude.”

I went to see Gallivan’s “Sassy Gay Friend Comedy Show” with a friend at the Second City Theater training center in Hollywood last Friday night. The venue is nothing particularly glitzy, but the walls are lined with images of Second City’s greatest throughout their careers, including John Belushi and Tina Fey.

Once inside, the stage is cozy, warm, and inviting. The music of choice, Kelly Clarkson, pulses through the sound system. And then the lights turn down, and for those of you who have watched the SGF videos before, the familiarly structured narration begins: “This is Lady Macbeth. She is waiting on her husband to kill her king...”

And then with a leap and a cry and a swish of an orange sequined scarf: “WHAT. WHAT. WHAT ARE YOU DOING.”

Gallivan’s show was, predictably, a reiteration of several of his Youtube skits, but he also included Sassy in new roles. He invited audience members onto the stage to talk about relationship problems as Sassy, and also to coo over them, remarking on one girl’s glittery shirt, “Oh, that’s like catnip for a gay man.”

One of the highlights of the show was when one girl told him about her long-distance relationship with a boy she had met at acting camp, and Sassy pursed his lips and said, “Oh girl… you know.”

Separating his onstage persona into himself and “Sassy” allowed him to transition between the two roles because, well, they are two separate roles. Gallivan’s real voice is nothing like Sassy’s higher-pitched “Oh no you didn’t” parody; in fact, the opening narration of his videos and his skits is done by him.

Gallivan took some time out to do his own material, and it was every bit as hilarious as his other self’s dialog. Under the pretense of taping his own literature show for PBS (“I always thought it had meant ‘Pretty Boring Sh*t’”), Gallivan told the audience a little more about himself: 41, gay, an ex-middle school English teacher.

He did a song and dance (“I thought to myself, what would be the gayest way to do this?”) about the awkwardness of being attracted to younger men, framing the two men he sang about as former students of him. He cursed several times, every time yelling to the backstage, “I’ll pay the fine.”

But Gallivan also described how he came out to his family, and their reactions to his revelations (“My older brother still calls me and asks, ‘Hey Brian, you still gay?’”). In a particularly poignant moment, he simulated the toast at a gay wedding, made by one of the groom’s father.

Gallivan’s sexual orientation is still a serious issue for him, although he heightens it to hilarious use on the stage, such as when he riffs on things like “sexual orientation conversion camp”: “Maybe God couldn’t hear our prayers to become straight, because we were too busy sticking our tongues into each others’ mouths.”

I went to see only the second time Gallivan did his show, but he will be at the Second City Theater every Friday at least through October.

The premise of the show is based on the fact that most of the viewers will have already watched the SGF videos online, and probably already quote Sassy’s catchphrases and bon mots (ie “Slow down crazy, slow down”).

But while some of the material will be extremely familiar, the most memorable parts of the show came not from Sassy, but Brian. A wryly smiling and towering figure, he may not be super sassy in real life, but yes, he has plenty of advice to give, and he doesn’t have to be wearing an orange scarf to be dishing it.

Reach Staff Reporter Lilian Min here; follow her on Twitter here and on Google+ here.