Internet Gold
(The early internet: where Caleb's humor was forged)
Books Caleb Actually Finished
(A loving nod to the rare few that made it all the way to “The End.”)
Obscure Music
(Yes, these are real songs. Yes, he knows every word.)
1998 Called
Double Jeopardy
(The category for trivia champions, Jeopardy junkies, and people who memorize lyrics for no reason.)
100

This phrase, popularized on Vine, is a timeless tribute to the best type of humor: “...I coulda dropped my what?”

What is croissant?

100

This title is what Caleb might call himself, seeing his bookshelf more as a display of potential reading rather than evidence of actually finishing any books.

What is a “book collector”?

100

This classic Billy Joel song lists historical events rapid-fire—Caleb once knew it word for word, which is both impressive and unnecessary.

What is We Didn't Start the Fire?

100

Caleb's birth year also gave us this browser-destroying music video featuring Cher.

What is "Believe"?

100

In the echoing halls of Playstation, Caleb’s chaotic alter ego (name not exact) struck fear with this self-deprecating tag.

Newbie Kanoobie? I forgot how to spell it!

200

Caleb’s memes come from this chaotic, pre-TikTok app that peaked in 2012.

What is i-funny?



200

This tearjerker taught Caleb that dogs, like childhood, must eventually go to the big red fern in the sky.

What is Where the Red Fern Grows?

200

Caleb has never related to the title of this chaotic Jon Lajoie song, but he has memorized every word.

What is High as F%#K?

200

This boy band dropped their debut U.S. album in 1998, launching a million frosted tips and teen heart attacks.

Who are NSYNC?

200

If it’s a piece of random trivia, Caleb knows it. If it’s his great-great-uncle’s cousin’s cousin, he also knows it, thanks to this intense hobby.

What is amateur genealogy (aka family tree sleuthing)?

300

This 6-second app was the birthplace of “Road work ahead...uh yeah, I sure hope it does” and Caleb’s chaotic sense of humor.

What is Vine?

300

The book series that made Caleb a time-traveling historian before he could spell “Renaissance.” 

Hint: Author Mary pope Osborne write about Jack and Annie while they traveled through time in all of these, making history more exciting than recess. 

What is The Magic Treehouse?

300

This TikTok-viral country murder ballad is both disturbing and somehow... catchy?

What is Psycho by Jack Kittel?

300

On April 13, 1998—the exact day Caleb was born—this U.S. president held a press conference in which he definitely did not mention a certain intern.

Who is Bill Clinton?

300

This pest hides in the soil and was Caleb’s nemesis during his sweet potato research.

What is a nematode?

400

“Can I get a waffle? Can I PLEASE get a waffle?” was shouted in the middle of this iconic southern restaurant brawl.

What is a Waffle House fight?

400

This Civil War novel may be the reason Caleb could pass a history class with only literary references.

Hint: This book follows a young soldier's journey of fear, courage, and self-discovery during the American Civil War, but don't expect any literal "red badges" — just a lot of internal conflict. 

What is The Red Badge of Courage?

400

“You can get anything you want…” except a short song. Caleb insists this 18-minute anti-war song that somehow involves littering is a Thanksgiving essential.

What is Alice's Resturaunt by Arlo Guthrie?

400

This band made 1998 feel like an emotional therapy session with their angsty hit “Iris” — which still plays in 73% of CVS stores today.

Who are The Goo Goo Dolls?

400

Caleb took apart electronics for fun as a kid. He usually forgot to do this afterward.

Put them back together. :\

500

This Vine, which features someone standing in front of a large group of birds, became iconic for the line, "Look at all those _____."

What is "chickens"?

500

Caleb may or may not have read this Orwell classic, but he definitely had opinions about pigs afterwards.

What is Animal Farm?

500

In this Jim Stafford tune, Bill may or may not be Caleb’s girl. Or his guy. Or both.

What is My Girl Bill?

500

This influential tech product launched in 1998 and revolutionized portable music, paving the way for future devices like the iPod.

What is the Walkman?

500

Caleb can almost perfectly recite all the U.S. Presidents in order thanks to this dinnertime educational tool.

What are presidential placemats?