Jeopardy Ain't Always Bad

A Week in the Life of a Person Who Won an Episode of Celebrity Jeopardy (plus, an invitation to join next week's office hours where we'll digest the inauguration)

I found my trailer.

Last week Celebrity Jeopardy kicked off its third season, and I won the premiere episode! I was up against actor Max Greenfield (CBS’ The Neighborhood and Fox’s New Girl) and Camillla Luddington (ABC’s Grey’s Anatomy). The episode didn’t air live, so I’ve been holding this secret from you all for a little bit. I hope you understand.

I never know how people will respond to anything I do. I am hopeful, but also reserved because there are unexpected surprises. Someone always gets mad at something in whatever I do. I’ve learned to roll with it… mostly. But this being-on-Jeopardy thing has been an overwhelmingly pleasant experience in the midst of so much awfulness going on in the country.

It is funny how different it is being on regular TV—one of the original three network channels—than it is being on a cable channel or a streaming service. I heard from relatives and friends I rarely talk to who saw it. One of my mom’s friend’s who probably hasn’t seen me in over 30 years reached out to her saying how proud she was of me. My middle kid and I were walking in Oakland, and a man yelled, “Good job on Jeopardy, bro!” A man who was with him said, “Who was on Jeopardy???” He turned and saw me and looked at me like he wasn’t surprised. My middle kid and I had fun for the rest of the day doing our impression of Good job on Jeopardy, bro! So much for Oakland being a doomloopian hellscape… or a hellescapian doomloop. New slogan time. Oakland: City of Compliments

I even heard from two-time Jeopardy winner Robin M. Swartz on Instagram.

While Jeopardy only aired twice on ABC (on Wednesday and Saturday), it was on repeat in my house. My mom came over and watched after she had already seen it. My two youngest daughters and I watched the episode at least three times. They started answering the questions in advance, as if they hadn’t seen it before.

Then this past Tuesday, I went to San Quentin Rehabilitation Center (the place formerly known as San Quentin prison). I was there for the graduation of the first cohort of men who had participated in the Back To The Start program. Back To The Start is a program that teaches biographical writing to the men in prison there as a way to help them better understand their lives. It was a powerful day. I felt lucky to be there. I am a member of the advisory board of Back To The Start, and I spoke a bit about why I wanted to be on the advisory board. Then I moderated a panel with policy makers, an activist, and a lawyer. It all took place in their chapel. And then we all ate the same lunch that the men of San Quentin ate. I had a cold ham sandwich with mayo, a slice of government cheese, and iceberg lettuce. There was also potato chips, a bottle of water, and a cookie. I was starving. It was delicious.

Since I have been going to San Quentin on and off since 2015, I’ve gotten to know some of the men over time. It is strange to feel so familiar with people I have seen only a handful of times in life. When I walk through the gates at San Quentin, the greetings begin immediately. But Tuesday, the greetings were different. Everywhere I turned one the men would say, “I SAW YOU ON JEOPARDY!”

I had no idea that they had access to Celebrity Jeopardy in San Quentin, and I had no idea that they would be interested in watching it. Not only did they have interest, they were excited to see me on it. Many had paid close enough attention to be able to tell me that they were happy I had come from behind for the win. “I thought you weren’t gonna do it. But you did!” These men—many of whom are in prison rehabilitation center for life—were clearly proud of me. It was amazing and slightly overwhelming. It was also very heartening.

I heard about my Jeopardy appearance all day from various men. I also heard that they had seen me on TMZ when I was on to talk about the San Quentin Film Festival. Some had even seen themselves on the TMZ segment. It was apparent that it meant a lot to them to be talked about and seen on television. It was special that this comedian guy, who had been to San Quentin a few times, wasn’t forgetting about them when he left San Quentin. Whenever I’m asked to go on TMZ, I question if it is the best platform for me. But I will do that no longer. And the response from the men at San Quentin reminds me to speak about them more often.

Later that night, I was with my family, having dinner in Berkeley. A woman walked into the restaurant and said she had seen me on Jeopardy. She told me she was hoping I would win that episode, and she was pulling for me in the rest of the tournament. I thanked her for watching, and then she dropped the bomb. SHE HAD WON ON JEOPARDY IN THE LATE 80’S! Her name is Sandra Gore. She won five days in a row, which was the maximum days you were allowed to win on Jeopardy at that point. (They have since changed the rules.) At the time, it was the longest a woman had ever won on Jeopardy. She appeared on other episodes of Jeopardy throughout the years. She said her Jeopardy winnings helped her move to California. Sandra and I chatted a bit, and then I did something I rarely do when I met a fan on the street. I ran and got my camera so I could get a picture.

This Jeopardy thing is an incredibly cool club to be (sorta) in! And what unpredictable but delightful ripple effects to see from it. I will be back on the show, in the semi-finals, on April 2nd. It’s nice to have something to look forward to as this year kicks into high gear next Monday, on what happens to be both Inauguration Day and Martin Luther King Jr. Day. That day will invite us to look both backwards and forwards at the same time. Remember when Trump and his ilk say, “Make America Great Again,” that MLK died trying to Make America Great For The First Time. Talk about a stark difference. A whole different kind of jeopardy.

January Office Hours on Tuesday 1/21

Speaking of the inauguration, let’s talk about it next week. Save the date! Join me for Office Hours on Tuesday, 1/21 from 11am - 12pm PT / 2pm - 3pm ET. We’ll meet on Zoom and talk about what went down. I’ll send a zoom link to all of the Who’s With Me? paid subscribers on Tuesday morning.

My monthly Office Hours on Zoom are one of the perks for paid subscribers. If you’d like to join, you can upgrade your subscription here:

You’re With Me

I’m Going on Tour
The 2025 Stand-Up Comedy Tour

You asked for it. Or maybe you didn’t, but I’m about to go back on the road to do stand-up. After a 2024 run at The Berkeley Rep and an incredible show in Davis, California, I’m heading out on he road to do stand-up comedy in 2025. These hectic times demand some jokes, written hectically while I’m also trying to raise three kids.

Tickets are now on sale for the first leg of the tour. (The tour doesn’t stop here. I’ll announce more cities soon!)

Want to Show Up for LA?

Remember my friend Kate Schatz? We wrote Do the Work! An Antiracist Activity Book together. Well Kate also has a fantastic Substack newsletter called I Love What You’re Doing, and this week she sent out a list of practical things you can do to help people who have been impaced by the fires in LA. Check out this compliation of resources and subscribe while you’re at it.

California Love

Please consider sharing or donating to Victoria Valentino’s GoFundMe, too. Victoria Valentino is a singer, actress, and ex-Playboy Magazine centerfold, back when Playboy Magazine was PLAYBOY MAGAZINE. She was the first survivor of Bill Cosby that I interviewed for my docuseries We Need To Talk About Cosby. Our showrunner, Katie King, shared that Victoria's apartment burned down. She is fine, but she lost everything. Victoria’s friend started a GoFundMe to help Victoria replace the things that can be replaced. I encourage you to spread the word and/or donate what you can to this kind warrior. Without the generous contribution of her time and her story, my work on that series is undone.