Bo,
Normal (haha) famous people always pretend like their lives are so glamorized and important, but you knock your audience members with “don’t woo for me. You don’t know what’s next”. You're right. It's like the element of surprise.
The one major thing I appreciated about your Make Happy show (now on Netflix) is how it makes light of mental illness. Normally when listening to a song called “Kill Yourself”, many people would be thrown off by the title (and the suggestions, really). But after continuing in the routine, you sing: “Come watch just some skinny kid with steadily declining mental health”
Using humor to address mental health seems to be a fleeting idea lately, but many of the comedians I see do not have such delicate and personal handling of their mental health (who really does?). Talking about mental health is such taboo, and when people hear that you have depression, anxiety, or other mental conditions, they suddenly treat you differently. I am the same way with comedy: I use self-deprecating humor, but it makes people happy and laugh, even for a minute. Many people don't make fun of their mental health.
Your bit: “I don’t think that I can handle this right now”/Kanye rant (so good) is something so real. All of the time, people act like small-mouthed pringle cans and overflowing Chipolte burritos are their biggest problems; but when you are constantly wondering what your purpose is in life or even if you should keep going, there are bigger issues in the world, like suicide and lack of clean drinking water.
But you talk about “making happy”. Like you said, you may have privilege and fans, but it’s really hard to make happy. I am constantly hearing people say “I want to be happy” or “I am happy”, but then realizing how hard it is to make “happy” or stay happy, because it’s such a fleeting thing. And what people don’t understand about happiness is that they have to make it. I have never had happiness handed to me (and medication [happy pills] certainly isn’t a way to suddenly ‘be happy’). People don’t realize that you can’t be happy all of the time, and your stand-up is a way to channel that. You have serious moments and you have hilarious bits, but you make fun of everything under the sun’: you bring light to such serious issues in such ironic ways, that people who do not understand your style of comedy would not get the show. :"I want to stay true to myself". As do I.
And thank you for helping me decide to “make happy”.