Many of us look back at 1999 as the dawning of the modern golden age of women’s tennis, a season that saw four different Slam champs, the abrupt exit of one GOAT, and the breakthrough of a new one. Lindsay, Martina, Venus, Serena, and Steffi battled for the biggest titles and crafted historic, enduring storylines at every major event of the year. There was a changing of the guard, sure, but the shift from one era to the next is never quite as cut-and-dry as it seems. Plus, of course, the memes -- or, in this era before memes -- the off-court controversies and clownery that we still talk about: BeadGate, the formal education argument; and more darkly, the homophobic insults thrown at Amelie Mauresmo and the persistent, racialized "muscles vs. brains" narrative. Let’s take a walk down memory lane and discuss a season of women’s tennis that quite literally changed the sport forever.

03:10 Setting the scene: What is happening in women’s tennis and the culture at the fin de siècle? What does the teen pop explosion and Y2K have to do with tennis?

08:10 The WTA’s struggles with investors and why anonymous “analysts” doubted the marketability of women’s tennis

19:30 So what makes the ‘99 season so special?

22:55 Themes of the season: the Williams sisters are coming, and not everybody’s happy about it

29:55 Martina is #1, but the dominance is slipping

37:40 Australian Open: Hingis three-peats, Mauresmo comes out, and we endure BeadGate

55:25 Roland Garros: Graf wins final major in an almighty mess of a final

62:50 Wimbledon: Lindsay ain’t just a hardcourt wonder

69:45 Steffi calls time on one of the greatest careers in tennis history

72:25 US Open: Serena bags the first Williams singles Slam, beating a befuddled Hingis in the final; plus, why the ‘formal education’ dust-up is even more instructive than we remembered

83:50 The year-end rankings, some fun facts about the Slam season, and the signs of what’s to come