Andy Richter Dances (Talks) With The Stars (Me)

Plus, please help me to help you to live Your Best Life In Hell

Apr 27, 2026

My friend Andy dang Richter is on the podcast

So I realized that I’m in the tenth anniversary year of podcasting about mental health and one of the first guests I ever had on The Hilarious World of Depression was Andy Richter. You know him from his position as Conan O’Brien’s literal right hand man as well as a deeper run on Dancing with the Stars than anyone, including Andy, expected. I’ve talked with Andy plenty of times between then and now and knew he had gone through a lot, notably the end of a long marriage and big career changes with Conan’s TV talk show ending.

What interested me is that when we spoke ten years ago, the depression that dogged him for quite a while was largely under control thanks to medication, talk therapy, stable home life, and a steady career. So where is he now?

Back in a good place, he says, after some choppy waters. The divorce was tough but so was the marriage that it sounds like he decided to end. He yo-yoed (sp?) on his weight, entered the online dating scene to varied degrees of success, but ultimately met Jen, who he married, adopting her young daughter Cornelia in the process. You’ve seen his family if you watched Dancing with the Stars (a TV job, he says, that paid well so he took it because that’s his line of work). He had some dances with Cornelia and his son, Will, from his first marriage, was there for nearly every taping.

Something I love about Andy, why I had him on the old show right out of the gate, is that he’s a straight shooter. He’s nice, he’s kind, he’s ethical, sure, but there’s nothing all that sugary about him. If something is bullshit, he’ll call it that. If something pisses him off, it’s usually for good reason and he’ll say so.

Andy Richter is kind of an ideal guest for the kind of show I set out to make ten years ago and am still making today.

WITH YOUR SUPPORT. (how’s that for a transition?)

It’s still the Max Fun Drive! But this is the LAST regular newsletter of the Max Fun Drive!

Okay real quick: you can join Depresh Mode at the $5 in a new, super-simple method by clicking here. Or Sleeping with Celebrities the same way here.

Or if you want to join BOTH or other shows too or at higher levels (yes, please), you can go to the regular dependable link.

Why do we need to have a drive every year? Are we just getting richer and richer?

No. There is attrition. Our operating budget is always smaller just before the drive than it is after a drive. People’s lives change. Sometimes they can’t afford it anymore. Likewise, we’re always getting new listeners and so we need to explain to them that the only way Depresh Mode, Sleeping with Celebrities, and all the other Max Fun shows exist is from the support of listeners.

So we ask you to pay for what you use.

A reminder:

The show’s creators own the shows. So I own the two shows I host. That’s huge and that’s rare. That’s why I couldn’t continue The Hilarious World of Depression after I got laid off. I didn’t own it. That issue is a big reason why I team with Max Fun, a place where I am not an employee.

Max Fun is a worker-owned co-op. They don’t really have employees. Just a lot of owners. That’s an amazing arrangement in today’s media landscape. Another great reason to support it.

And listeners support it. We sell some ads, not a lot. I don’t have any grants. It’s overwhelmingly listener-driven. It’s people deciding that the work we do constitutes a public good and a personal benefit.

Let’s build Your Best Life In Hell

The world is a scary place right now. To save time and space, imagine me gesturing broadly. So if you’re more depressed and anxious than before, oh, the 2024 election, consider that it’s a rational response to, you know, Hell.

At the start of the drive, Depresh Mode set out to hit 450 new monthly contributions. As of RIGHT NOW AS I TYPE THIS, we’re at 157. If we get 293 more, I will be able to create a limited run series called Your Best Life In Hell.

It’s a look at mental health that factors in your response to the world at large - politics, society, fascism, climate change, all of it - and formulates a plan on what to do about it. Not just interviews but a how-to. An approach.

That’s a heavy lift. I’ll need to bring help on board and pay those people what they’re worth. I can do it with your help. It can help you and help others and that’s what we’re about. That’s why we want your support.

The Winter of ‘26 in Minnesota taught me that if we help each other out, use the tools available to us to make contributions in concert with one another, we can make a huge difference. Please help us to our goal.