I found Bookers to hard core.
I would suggest Four Roses Single Barrel, Knob Creek or Elijah Craig 12. At your budget, I suggest getting all three, or possilby a large bottle.
Like the knowledgeable BoubonV said, you can get great bourbon for less money. The bottles I suggest are great, but come in stylish bottles, which I think is important when giving a gift. But the man is right Beam Black, Very Old Barton 100Proof, Fighting Cock, Old Forester are great but come in plain bottles.