xanyland Episode 9: Laughter and Life Lessons with Drew Dunn
In this episode I sat down with comedian Drew Dunn. Funny guy, new dad, and seemingly flawless human being. Drew shows a level of healing, understanding, and sense of self I rarely see in any person. How did he get so awesome?!
Drew made a name for himself in the stand-up world when he started competing in comedy festival circuits all over the place. He won the Boston Comedy Festival in 2017, and launched into a series of consecutive wins followed by the Seattle International Comedy Competition in 2018 and finally being selected to be a “New Face of Comedy” at the prestigious Just for Laughs Comedy Festival in Montreal in 2019. He has his own special on Dry Bar Comedy and opened for Dane Cook on tour in 2023 and 2024. He is just getting back to touring after having a baby 4 months ago! So congratulate him by watching his shit online. Or better yet go see him on tour now in a city near you!
Drew is I think my first guest who is not actively in therapy. He comes from a large family, 1 of 7 kids (mostly boys) and is also very close with his wife’s family. Big green flag fact about Drew — he has been with his wife since they were 17. High school sweethearts is INSANELY MAGICAL and RARE. I only know one other couple like this and it’s my brother and his wife. Generally Drew seems super close with all his family, blood, in-laws, friends, all of the above. Can I study these people because they must not be real. As an avid fan of object relations theory which is the mother of attachment styles, my hypothesis is that he actually has healthy attachment!!!
We talked a lot about doing comedy and what success really means. Coming from a performance background myself, sometimes it can get confused and feel like someone else’s success is potentially taking an opportunity away from you. But Drew reminds us that ANYBODY’S success is a good thing for all of us. If people are successful at the thing you do, hopefully that makes more room for more people.
Drew said something that really resonated with me: think about how people found their success. Not why. Ask yourself how they figured out getting an online following, or how they found their success or tapped into a specific market. Not why did it happen to them and especially not why didn’t it happen to me. That’s unproductive and ultimately bad for our mental health.
We talked about careers, family, grief, loss, and a huge change in Drew’s life … fatherhood. Parenthood does deeply change you. Speaking from experience, there were anxieties that came with being a new parent that shaped the person I am today. Like oh shit I actually can’t die and leave this tiny being alone. I can’t afford to be reckless. My daughter is the reason I became a therapist. Drew says, “the future has a face now” and I concur.
This conversation with Drew was uplifting and easy, when I could get a word in. ;) He gave good advice on careers, fatherhood, dealing with grief, comedy in general, and even mental health. We love a man who will cry. I hope that episodes like these can be an inspiration to other men. Vulnerability is a desirable quality. Try anything and everything and figure out what you like. Trust yourself, work really hard, focus on things you love and get really good at them.
Thanks Drew, and again thank you for admitting to not being perfect towards the end of the pod. Which makes you appear even more well balanced.
Watch the episode below, or find xanyland on your favorite podcast platform.