Books, TV, and video games that I would recommend to anyone with high conviction (or are just my favorite in the genre). Part of my criteria is timelessness (could consume now or arbitrary point in the future for the first time and still enjoy/recommend).
Books
Life, or Top X Favorites:
How to Win Friends and Influence People by Dale Carnegie
Meditations by Marcus Aurelius (Translation by Gregory Hays)
The Lessons Of History by Will & Ariel Durant
Seeking Wisdom: From Darwin to Munger by Peter Bevelin
Antifragile by Nassim Nicholas Taleb
The Timeless Way of Building by Christopher Alexander
Leadership & Business:
Certain to Win by Chet Richards
High Output Management by Andy Grove
Zero to One by Peter Thiel
Extreme Ownership by Lief Babin & Jocko Willink
The Hard Thing About Hard Things by Ben Horowitz
The 1-Page Marketing Plan by Allan Dib
Understanding Michael Porter by Joan Magretta
Investing:
The Little Book of Common Sense Investing by Jack Bogle
The Outsiders by William Thorndike
Philosophy:
Stubborn Attachments by Tyler Cowen
Tribes: On Homecoming and Belonging by Sebastian Junger
Finite and Infinite Games by James Carse
Wanting by Luke Burgis
Parenting:
Mindset by Carol Dweck
Cooking / Food:
The Food Lab by J. Kenji Lopez-Alt
Fiber Fueled by Will Bulsiewicz
Other Non-Fiction:
A Short History of Nearly Everything by Bill Bryson
The Rise of Theodore Roosevelt by Edmund Morris
The Power Broker by Robert Caro
Liar's Poker by Michael Lewis
Literary Fiction:
Atlas Shrugged by Ayn Rand
Monkey Wrench Gang by Edward Abbey
All the Pretty Horses by Cormac McCarthy
Matterhorn by Karl Malantes
Stories of Your Life and Others by Ted Chiang
Exhalation by Ted Chiang
East of Eden by John Steinbeck
Sci-Fi:
Ender's Game & Speaker for the Dead by Orson Scott Card
Dune by Frank Herbert
The Three-Body Problem (Trilogy) by Cixin Liu
Starship Troopers by Robert Heinlein
Snow Crash by Neal Stephenson
Thriller:
Tinker, Tailor, Soldier, Spy by John LeCarre
The Day of the Jackal by Frederick Forsythe
Red Sparrow (Trilogy) by Jason Matthews
Kids:
Harry Potter (Series) by J.K. Rowling
The Phantom Tollbooth by Norman Juster
The Graveyard Book by Neil Gaiman
Redwall by Brian Jacques
Where the Red Fern Grows by Wilson Rawls
TV
Seinfeld
The Wire
Friday Night Lights
Halt and Catch Fire
The Expanse
Movies
No Country for Old Men
The Bourne Trilogy
The Departed
Jiro Dreams of Sushi
Moneyball
The Big Short
Games
Civilization II
Portal 2
A Dark Room
The Legend of Zelda: Breath of the Wild
Hades