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Look, this is gonna be a lightning round class today because this piece of crap Milton is knocking on my door and I ain’t ready to answer him just yet. 

What a week. God, I hate Hurricane season in Florida. It’s the worst. It’s also such a crapshoot. 

So, we left our house yesterday to come about 100 miles south to our hometown, where our entire family lives. Our town, DeLand, was supposed to get crushed pretty good, and I didn’t feel like being there when the power went out and a water oak smashed through the ceiling. No thanks. 

Of course, Milton jogged a bit south throughout the day yesterday, and it looks like he’s now gonna split the difference – gonna go straight through state and wind up somewhere in the middle of DeLand and Vero. So, better for my house – for now – but probably a little worse for where we are. 

Oh well. You play the hand you’re dealt and hope for the best. We’re here, we’re strapped in, I slugged down 8 Busch Lights while putting up shutters yesterday. We’re ready. As ready as one can be, I reckon. 

On that note, welcome to a Hump Day Nightcaps – the one where we check in with 67-year-old Vanna White, and 25-year-old Gracie Hunt, and go from there. 

Welcome to class, Vanna! And welcome back, Gracie!

What else? I’ve got Jim Cantore and Liuetenant Dan doing work in Tampa, Jon Gruden resurrecting his career, and I’ll also mock stupid Howard Stern for literally becoming such a loser of a human. What the hell happened to that dude? He used to be so cool and so normal. And now he’s just insufferable. 

OK. Let’s get this show on the road before I get hit with a tornado warning. Pencils up, it’s ‘Cap time!

The Jim Cantore/Lieutenant Dan crossover was insane

Luckily, Jimmy ain’t in Vero this week. He’s been here plenty of times before, but not for this storm. Unfortunately for our friends on the West Coast, he’s setting up shop over there for Milton. 

I love Jim Cantore in a way a baseball fan loves their home team announcers they grew up with. The voices of summer, if you will. 

I grew up with Jim Cantore in my living room every single year from Aug. through October. In a weird, sick, twisted way, Jimmy is comfort food for me. Guy just makes me feel safe. Don’t know why, but he does. 

Anyway, Jim ran into Lieutenant Dan over in Tampa yesterday, and tried to convince him to abandon his boat. For those who don’t know Lieutenant Dan … he’s an OG over in Tampa who has captivated the state for two days now because he said he was gonna ride out the storm on his boat. 

He also has one leg and said if he had to swim to safety, he can’t, because he’d just go in circles. Wild, but true. 

Anyway, Jim – and the Tampa PD – had to intervene to convince him to leave. After intense negotiations, I’m happy to report that Dan has left the ship:

I can’t get enough of these Jon Gruden’s TikToks

What a ride. What a human. Two schools of thought on this, via the internet streets: 

1) Leave Dan alone and let him live his life. It’s a free country and if he wants to ride it out on his boat, that’s his right. 

2) Get Dan the hell off that boat by any means necessary, he’s going to die, and we don’t need to knowingly let Dan die. That’s a bad look for society. 

I’m probably in the latter on this one. Look, I’m all for a feel-good story, and Dan actually floating to the top of the Tampa skyline on his boat during a Cat 5 and living to tell about would certainly qualify as a feel-good story. 

That being said, his logic seems a bit flawed. I’m no scientist, but it seems to me that if his boat capsized, and he could only swim in circles, that’s probably not a great spot to be in. Just my two cents. 

Do love his attitude, though. Wonder who he’s voting for next month?!

Speaking of absolute wild cards on the internet, let’s check in with Jon Gruden for the second time in as many weeks!

Insufferable Howard Stern has plummeted, but a couple other 90s stars are THRIVING

I mean, my God. I don’t know what’s happened to Gruden these past few weeks, but I’m ALL IN, baby. If you scroll through the rest of his TikTok, it’s just a bunch of semi-normal Xs and Os videos with Gruden. 

But he’s recently taken on this alter-ego of “Feelin’ Nicey” football guy, and I think he’s really onto something now. We just have these two videos of Mr. Nicey, but I have a feeling we’re about to get plenty more. How is this guy not back in the league? I’d get in a foxhole with him any day of the week. 

Shred ’em, Stroud! 

Heat ’em up, Mayfield!

I LOVE this character arc for Jon Gruden. Awesome job by the scriptwriters here. They nailed it. Need one of those shirts STAT. 

OK, rapid-fire time because, well, you know. 

First up? Let’s check in with Howard Stern!

First off, and I don’t do this often (ever), but credit to Kamala for having a shred of a sense of humor. A shred. Thank God. I hate SNL, but the Maya Rudolph/Kamala impersonation is maybe the best thing that show has stumbled upon in years. Kudos. 

As for Howard, he’s such an unbelievable loser at this point. It’s amazing, really. COVID really melted his brain. Trump did, too. Obviously. 

“I don’t want you to be made fun of.” My God. His downfall will be studied for decades. It’s important to find out exactly what happened so we can avoid it moving forward. 

Next? From a 90s star who is now a shell of himself to a couple of 90s ringers who have aged like fine wine! First up? Lindsay Lohan!

Lindsay Lohan finding her second wind in life after she went through the predictable 90s star downfall in the early 2000s has been such a pleasant surprise. You see too many of these stories end poorly – hey, Britney! – but not Lindsay. She’s back to her old self and thriving. 

And a Parent Trap throwback? My God. She knows the way into my heart. One of the best summer movies of all time. There, I said it. 

And you also get Dennis Quaid – AKA Ronald Reagan! Win-win. 

Now, to another 90s heartbreaker who is still pumping out heaters at 67 … Vanna White!

Gracie Hunt takes us home

Vanna! God, I remember back in the day when Vanna White was all anyone could talk about. She was such a superstar when she burst onto the scene. Feel like she was on the cover of every single TV guide growing up. 

Yes, TV Guide. Look it up, kids!

OK, that’s it for today. Let’s have Gracie take us home. 

Be safe. Talk soon (maybe not tomorrow but soon!). 

OutKick Nightcaps is a daily column set to run Monday through Friday at 4 p.m. (roughly, we’re not robots).

You ready for Milton? Email me at Zach.Dean@OutKick.com.