I decided that I was going to go with some Cubs and Blackhawks shirts (his favorite teams), some of his favorite candy, a few giftcards to places he likes, and his favorite drinks.
After putting a bunch of shredded paper in the bottom I just started filling it up. I found the cutest little baby bottles of beer which is like 3 drinks for him but they were seriously so cute I couldn't resist. He seemed to like it and it was a fun gift to put together. So just remember if you are having problems deciding what to get your guy, this "man basket" is a go-to gift!