I was going through some shit the other day and happened on the June 1999 Playboy issue. It may be the finest Playboy ever. The cover/feature was PMOY Heather Kozar. The centerfold was Kimberly Spicer and the other feature was The Pussycat Dolls. Also included was a fantastic interview with Sam Jackson right before Phantom Menace came out. There was also an interesting 20 questions with Christina Applegate.
Can you do better than that?