Of course I’m always initially inclined to say “ALL OF THEM! THEY’RE ALL AMAZING!” when someone asks this, but that’s not really helpful at all, is it? I think when choosing a book of his, it helps to narrow it down by what you’re into. I feel like Henry has generally made two types of books in his career. One is more diary-like, poetic, (sort of) fictitious short stories mixed with a bit of his own thoughts and experiences. If you’re into that, I’d recommend something like “The Solipsist”, “Roomanitarian”, “The First Five” and “The Portable Henry Rollins”(the latter two being great as starers since they’re both compilations of his previous work). The other type of book is his more journal-like material that mainly documents his experiences while traveling(“Smile You’re Traveling”, “A Mad Dash”, “A Preferred Blur”, and “A Dull Roar”), making a record(“Broken Summers”), or touring(“Get In The Van”, “See A Grown Man Cry/Now Watch Him Die”). They’re all great in their own special way and I think every Rollins fan has a different personal favorite.

You can get all the ones I listed on his website, by the way. I know getting a hold of his books in stores or other online retailers can be a bit tricky, so that’s the one place I would recommend buying them. He has a bundle of his last three books for sale right now(here), if you’re into that kinda thing.

So, yeah! I honestly don’t think you can go wrong when it comes to his books, really. He may not be a literary genius, but he can keep you engaged no matter what the subject is. He’s good at that kinda thing.