Beowulf fucking slaps
Books
Book reader community.
I've tried to like a lot of old books, and just never got them (or, sometimes, even got through them). Inferno, Don Quixote, Canterbury Tales, The Iliad, etc. I think the oldest book I've actually enjoyed was Dracula. Then there's a long drought after that; I think the next-oldest books I enjoyed were Harry Harison's Deathworld (1960) and Morris West's Tower of Babel (1968). West's book, particularly; I didn't realize it was that old until I finished it and caught a glimpse of the copyright date. It reads a lot like a modern spy thriller.
Not the oldest I’ve read, but the oldest I’ve properly enjoyed is Jane Eyre (and it happens to be my fave of all time too)
Probably something by Jane Austen? Actually technically Shakespeare but that was for school so it doesn't really count.
Beowulf
Dead Souls by Nikolai Gogol I'm a huge fan of 19th century Russian literature, and that is probably the oldest book I've read in that genre.
Other than that, I think Don Quixote is super fun to read at the start, but it drags on too long to be enjoyable all the way through. But that's the oldest book out of which I got a lot of enjoyment.
Dunno if you'd count it as a book but the Epic of Gilgamesh is one of my all time favorite stories that I regularly go back to. Also, predates Homer by a long shot.