I won Celebrity Jeopardy!

And that is the second best thing that happened to me last week.

The cat’s finally out of the bag! I am the winner of season 3 of Celebrity Jeopardy! When I say “finally” I mean finally. I’ve been holding this secret since the finals were taped in November 2024. I hope you all forgive me for not telling you. I was sworn to secrecy. (And I’m guessing I signed stuff saying I couldn’t tell.) It has been slightly maddening to regularly talk about being on Celebrity Jeopardy! and not be able to say, “I’M NOT JUST ON IT. I WON THE WHOLE DANG THING!” But now that our national nightmare of not knowing who is the winner of Celebrity Jeopardy! is over, I can confirm that it is ME! I am officially the title-holder of America’s smartest celebrity. “Smartest celebrity” is kind of the equivalent of being the strongest two-year-old. But seriously folks. I’ll be here all week. Try the veal.

Being the “strongest two-year-old” on Celebrity Jeopardy! means that the million dollars I won will support America’s public school children. I played for the organization DonorsChoose, where public school teachers and administrators raise money to pay for school supplies, musical instruments, field trips, and other things that should be paid for by the government! I have talked about how awesome DonorsChoose is many, many times here, so you can only imagine how happy I am to be able to help them get so much money for the school children of America. From now on, I’m the Secretary of Education! If Trump’s choice, Linda McMahon, wants the title back, she can fight me for it. After all, as the former C.E.O. of World Wrestling Entertainment, Linda has way more experience fighting than she does educating.

You can watch the entire season of Celebrity Jeopardy! on Hulu.

Me and my new trophy! We plan on honeymooning in New Zealand.

Honestly, though, it does feel awesome to win. I was just honored to be invited on. (“WHAT?! I’M A CELEBRITY???) During the first episode, my goal was not to embarrass myself. However, as my wife is well aware, I do know a lot of random things. In any conversation that gets stuck over an unknown fact or figure, I’m the first to pull out my phone and look it up. Despite my reputation of being singularly focused on racism and the liberation of all oppressed people, my interests are pretty eclectic. I joked about Wikipedia on Celebrity Jeopardy!, but I probably spend as much time on that website as any other.

Weirdly, I was most recently on actor Stacy Keach’s Wikipedia page. I was helping my ten-year-old, Juno, with her homework, and she mentioned that Jane Seymour had been the wife of King Henry VIII. I was immediately sure she had confused something because Jane Seymour is an actress and not nearly old enough to have been married to Henry VIII, so I looked it up on my phone to correct her. Turns out that Juno was right. Henry VIII was married to Jane Seymour… a different one than the actress from Dr. Quinn, Medicine Women. After learning this, I was curious to see if the actress was named after the Queen. Somewhere along the way I saw that the actress had been married to a man named James Keach, the younger brother of actor Stacy Keach. And then I was like, “I wonder if Stacy Keach is still alive,” so I went to his Wikipedia page. WELCOME TO HOW MY BRAIN WORKS!

(Stacy Keach is still alive, by the way. And the actress Jane Seymour chose that name in honor of the Queen. She was born Joyce Penelope Wilhelmina Frankenberg. Now you, too, have random knowledge!)

While I didn’t study for Celebrity Jeopardy!, per se, I have been jamming my head with random knowledge my entire life. That meant that when I won the quarterfinals episode–up against Max Greenfield from the sitcoms New Girl and Neighbors and Camilla Luddington from Grey’s Anatomy–I already felt like I was in the bonus round. In the semifinals (the second episode taped just a few hours later than the first one 😬) I was competing against Jackie Tohn, from the Netflix shows Glow and Nobody Wants This, and my friend, the legendary stand-up comedian Margaret Cho. Margaret had come ready. Apparently she had watched yeeeeeears of Jeopardy! episodes to prepare. I have never seen Margaret that serious in all the time I’ve known her. It was a bit intimidating.

The only thing that stopped Margaret from winning our episode was that she swung for the fences on every Daily Double. Margaret did what is called in Jeopardy! parlance “a true Daily Double.” That is where you bet all the money you have in order to double up. It is very risky, but true Jeopardy! fans love it when contestants do it. Margaret missed a Daily Double later in our episode, which put her in a really hard spot as we went into Final Jeopardy! While I had found a few Daily Doubles in my time on those two episodes, I never had the courage to go full-on “true Daily Double.” (In the first episode I only bet five bucks on a Daily Double.)

In literary terms, that ended up being a little bit of foreshadowing.

The final episode, which aired last Wednesday, was a roller coaster of emotions for me. I was up against Robin Thede, a comedian and producer who is best known as the creator and star of the Emmy award-winning HBO comedy show A Black Lady Sketch Show and David Friedberg who has a podcast.

I am really grateful to the Jeopardy! folks for letting me bring my wife Melissa and my two youngest daughters to the finals with me. (My oldest had rehearsal that day.) On the way to the show, my ten-year-old asked me about how Jeopardy! worked. I explained the whole you-have-to-answer-everything-in-the-form-of-a-question thing. To further explain how it worked we came up with a whole category all about Juno’s favorite musician/actress/person Olivia Rodrigo. If you don’t know about Olivia (or are Team Taylor Swift), then let me give you the highlights.

Olivia Rodrigo is a 22-year-old singer and songwriter who exploded out of the Disney Channel factory and into mainstream success. Before her current career as a 3-time Grammy-winning popstar, she was best known as one of the teens in the ensemble musical TV show with the best name ever, High School Musical: The Musical: The Series. It was must-see TV for the tween and teen set (and parents like me and Melissa) from 2019 to 2023. Before that, Olivia starred in the tween sitcom Bizaardvark, a show that was way funnier than it should have been but is also sadly (partially) responsible for Jake Paul. Ms. Rodrigo has two truly great pop albums out, both with a classic ‘90s alternative rock aesthetic. Juno’s first concert was Olivia Rodrigo’s Guts tour. Juno was so young that, when I told her I was taking her to see Olivia Rodrigo in concert, Juno responded, “YAY!... What’s a concert?”

I was so impressed with Ms. Rodrigo’s performance. She clearly is not a child star who is just trying to extend her career with music. She is a true singer-songwriter. She has pipes, and she is an electric performer with an eye for talent. A then-unkown Chappell Roan opened for Olivia Rodrigo on that tour!

This is kid who is both impressed by her dad and shocked to be on camera.

At one point during the finals, host of Celebrity Jeopardy! (and regular Jeopardy!) Ken Jennings asked me how I prepared. I told him the Olivia Rodrigo/Juno story. The audience thought it was appropriately adorable, especially when the camera cut to Juno sitting in the audience and smiling like, “Come on, Dada! Don’t embarrass me.” Then the unbelievable happened.

Later in the game, there was a category called “Hitmakers of the 2020s.” This answer popped up:

“Olivia Rodrigo broke our hearts with her first no. 1 hit, a ballad named for of all things – this government form of issued I.D.”

Even Ken lit up at the serendipity of it all. I buzzed in like my life and reputation (as a dad) depended on it. Luckily, I was first. I knew the question right away. I pretty much yelled it.

“WHAT IS DRIVER'S LICENSE?”

That is (of course) correct. And, before I knew it, I was given the next answer: a (duh duh duh) Daily Double. At that point, I was in third place. This Daily Double was the last clue of the second round of questions, a.k.a. Double Jeopardy!, right before we went into the third round of questions, a.k.a. Triple Jeopardy! I knew I had to make a move if I had any chance at actually winning. I channeled Margaret Cho.

“Let’s make it a true Daily Double.”

There was a gasp and applause in the audience. Sitting here, right now as I type this, I still don’t know why I had the courage to do it. The category was “Hit Makers of the 2020’s.” What did I know about hit songs from this area that weren’t written by Olivia Rodrigo? I’m mostly still listening to music from the ‘90s. Well that is true except for a song that I was obsessed with from summer 2024.

“He landed his fourth no. 1 hit in 2024 with ‘Not Like Us,’ a diss track aimed at Drake – Oh he also has a Pulitzer Prize, NBD”

The answer was so obvious to me that when you watch the clip you can see the look on my face that says, “You gotta be kidding me. I’m gonna double up with this???... Am I missing something? Is this a trick question?” Once I had confirmed with myself that this was really just a meatball served right over the plate, I answered.

“Who is Kendrick Lamar?”

Ken acknowledged that I was correct. To say I was excited is an extreme understatement.

The third round was mostly back and forth until the podcaster missed the last Daily Double, which was ironically about Denzel Washington—another question I would have known in my sleep. I couldn’t help but feel sorry for him… sorta.

Then it was Final Jeopardy! time. The category was “In Memoriam 2024.” I immediately started going over famous people who died in my head. Kind of a bleak way to spend a few minutes. When the answer was revealed, I was again sure I knew the question, but I was also pretty sure that Robin did, too, since it was about a famous comedian.

“This comedy legend always credited his wife Ginnie for the idea behind what is still called one of the greatest finales in TV history”

I knew it immediately. The show aired when I was a kid and I watched prime time TV with my mom. This was a great sitcom in an era of truly great sitcoms. It was set in a quaint hotel in Vermont. It had all the sitcom tropes: wacky neighbors, a will-they-won’t-they romance, and a central location that invited in lots of new characters. The comedy legend was Bob Newhart. And the last episode of the series is also legendary. It is basically a parody of the ‘80s soap opera Dallas and a callback to Bob Newhart’s first hit sitcom.

My only brief concern was, “Is it spelled Newheart?” Of course not.

I was the only one of the three of us who got the answer correct. The podcaster wrote a hello message to his kids. Robin thought the answer was Norman Lear, who was admittedly one of the people who had recently passed away that had gone through my head before I saw the actual answer.

Once Ken announced that I had won, I started to get emotional. Later on the Inside Jeopardy! podcast, I joked that someone must have been cutting onions for a lasagna, which is why I got teary. But of course it wasn’t true. On the podcast, I said I was happy for the children who were going to benefit from the money, but that wasn’t the only reason for the tears. I was also happy to have been able to do that with my family there, and it was so special to have this moment on TV with Juno. So much of my career happens with me on the road, away from my family, so it felt so special to have this huge moment with them being a part of it.

I had to hold in all that from November until last Wednesday. Whew!

The Olivia Rodrigo moment generated some chatter online. My friend, co-author, and fellow Substacker Kate Schatz created an amazing edit of the conversation with Ken about Ms. Rodrigo to me answering the Driver’s License question to get me getting the Kendrick Lamar Daily Double, and she posted it on Instagram. Kate’s narration and her cat add a special element to the whole thing. I decided to post and also decided—What the hell?—that I would tag Olivia Rodrigo in the post and see if she could just write, “Hi, Juno!” in the comments or even leave a heart on the post.

One day after I posted the video, I was in Chicago, winding down after a stand-up show, and I saw I had an IG message from… OLIVIA FREAKING RODRIGO! It was a video. She was talking directly to Juno. My mind was blown. It was so sweet and perfect. I have made these sorts of videos myself in my career, but – BREAKING NEWS – I’m not as famous as Ms. Rodrigo. I know she must be asked a million times a day for these things, so I know it is a big deal to make one, even if it doesn’t seem like it on the outside. It made me proud that Juno has picked such a great role model. Needless to say, Juno’s mind is still blown by this all happening. Even though her dad is in showbiz, this is a whole different level. She is still wrapping her head around the fact that THE Olivia Rodrigo knows her name and sent her a message. That is the best thing that happened to me last week. I’m tearing up thinking about it right now.

Okay, some other pretty great things happened last week. DonorChoose allowed me to use some of the one million dollars to wipe out all the current projects in the Oakland Unified School District and all the current projects in Mobile, AL where my dad lives. We are also using some of the money to match any donations made to projects in the cities where I do stand-up comedy. Currently, donations are matched in Chicago, my last tour stop, Bloomington, Indiana, where I’ll be this weekend. If you want to get in on the good feelings, make a donation to a project in Chicago or Bloomington, and DonorsChoose will match your donation using the Celebrity Jeopardy! winnings!

There are some more exciting plans for the money that we are working on. I can’t wait to tell you. Until then, check out those DonorsChoose projects in Chicago and Bloomington and use my matching donation. Let’s all be our own personal Secretaries of Education.

Who’s with me?

You’re With Me

But wait! There’s more Celebrity Jeopardy!

Here is a short podcast I did moments after my victory. I was still in a daze, as you can see.

And here is a collection of fun moments from the season.

Here’s a couple cool interviews about that last episode of Newhart.

I’m heading back to the Tribeca Film Festival and you won’t believe why. (I barely believe it.)

This year is the 30th anniversary of Martin Scorsese’s film Casino. You have seen me reference The Godfather on here, but I’m a huge fan of the film Casino too. I think it is underrated because it came out after Goodfellas, which is admittedly a more headline-grabby film. Both films also star Robert De Niro and Joe Pesci in roles as mobsters, but that’s where the similarities end for me. Last year, when I was at the festival, I mentioned to one of the programmers that I was a huge fan of Casino when she mentioned the upcoming anniversary. I said, “If you need me, put me in coach.”

Well, I’m in the game! June 5 at Tribeca, they are showing the film, and after the screening Robert De Niro and Martin Scorsese will be in conversation about the film with… me.🤯 You can get tickets if you are so inclined. And yes, I feel like Juno finding out Olivia Rodrigo sent her a message.

That’s Robert De Niro talking to me right before we go onstage.

Bloomington, Boston, and Ridgefield, CT, I’m headed your way!

Come out and see some stand-up! Here are the remaining dates for my Who’s With Me? tour.

Know Your Rights: Digital Privacy

On the latest episode of the ACLU podcast, At Liberty, I spoke with two digital privacy experts on how to keep your data safe and things to consider if you’re going to travel out of the country. This is a super informative conversation.