Man's Search for Meaning by Viktor Frankl. Anything by him, really.

Crime and Punishment - Dostoevsky

Siddhartha - Herman Hesse

While these are entertaining, they also have an element of applicability to real life, which is why I really enjoyed those books.

I enjoyed the Darth Bane series for star wars even though I otherwise wouldn't give a shit about Star wars books

It was a very good fiction read explaining how the sith became only a sith lord and an apprentice. One of the best backstory book series I've ever read

I recently finished LOTR. I'm 35 and hadn't read it.It was a very nice read, fully recommended

"Gates of Fire" by Stephen Pressfield.

I'll also agree with @MrSupreme that the "Lord of the Rings" trilogy is worthwhile (read, "The Hobbit" first).

The Old Man and The Sea. Or anything by Hemingway.

Animal Farm and 1984. I haven't read anything else by Orwell, but I can 100% guarantee those.

To Kill a Mockingbird.

Dune, if you like scifi. And, on that note, anything by Arthur C. Clarke and Asimov.

H.P. Lovecraft if you like fantastical, eerie stories. I'd tell you to buy the book with all his stories but, if you need some convincing, read The Case of Charles Dexter Ward.

Pride and Prejudice. Really. It won't be your favourite book ever, but it's worth the read (though that's probably Austen's only book I'd recommend).

Probably anything written by the russians - their take on how ruthless life can be is quite something. I'm sure there's a big debate on where to start, but I've been loving Nabokov's short stories.

One Hundred Years of Solitude. I always thought spanish was an ugly language until I read García Márquez. I confess I didn't really feel this book while I was reading it (and consider having pen and paper around to draw the Buendía's family tree) but, once I finished it, I spent the next week remembering it and slowly digesting the story. 10/10, would read again. But if you want something shorter, Eyes of a Blue Dog; and I've heard good things about Love in the Time of Cholera.

The Count of Monte Cristo. If you've liked any of the movies, let me just say that, compared to the book, they're shit. I've never seen one nail the story - and, most importantly, the ending. It's a long one so, if you want something shorter (but not as interesting), The Three Musketeers.

I like threads like these because the life a man leads should be more than just gaming women.

Ayn Rand - Atlas Shrugged (long but good), Fountainhead

Tom Clancy's original stories (he's dead and they're still releasing books in the "universe") - I'm talking about The Hunt for Red October, The Cardinal and the Kremlin, Debt of Honor, Clear and Present Danger, etc.

1984 and Animal Farm by Orwell - I read these in Junior High School and it's wild how much of it has come true.

Michael Connelly's books - They're mysteries based on the West Coast - If you've seen Bosch on Amazon Prime or "The Lincoln Lawyer" movie, they're based on his stories.

"Whatever" and "Serotonin" by Michelle Houellewhatdafeck.

Both dealing with masculinity in one form or another. Very introspective, not a lot happening action-wise. Yet, I found them both very hard to put away. Loads upon loads of brilliant observations.

"Do Androids Dream of Electric Sheep?" by Philip K. Dick.

I'm a sci-fi nerd, so I ate this one up in no time (it's pretty short anyways).

The "2001" series by Arthur C. Clarke. My number one movie, so good to know what actually happens towards the end. Even though I'd already watched 2001 and 2010, it was a captivating read.

Some very solid recommends in here already. You might think about starting a tribe called 'book club'? And get guys to post book recommends in there, with a short (50 word) summary of why they are recommending it. Just an idea.

Here's my list:

1984 (G. Orwell) Absolute masterpiece. One of the most important books of the 20th century. Surprisingly short. I went on to read every single book by G.O. - all are winners.

A Clockwork Orange (Anthony Burgess)

Do Androids Dream of Electric Sheep? (P.K. Dick)

The Grapes of Wrath (John Steinbeck)

The Lord of the Rings (Tolkein)

Brave New World (Huxley)

Old man and the sea (Hemmingway)

Crime and Punishment (Fyodor Dostoevsky)

A Brief History of Time (Stephen Hawkins)

The Forgotten Soldier (Guy Sager)

The Gulag Archipelago (Aleksandr Solzhenitsyn)

The unbearable lightness of being (Milan Kundera)

Money (martin amis)

The Trial (Franz Kafka)

If you want something lighter, I would add in anything by John Le Carre and also anything by Grahame Green (you will enjoy all of them!)

I really like The Iliad