“Are you sure you want it?” calls Andy Roddick to me from across the net one bright evening at Randall’s Island—“it” being Roddick’s blisteringly famous serve, which typically clocks in between 130 and 150 m.p.h. and has set records at Wimbledon, the Davis Cup, and the U.S. Open. A thumbs up, and Roddick lets it fly.

In blazing succession, two serves whiz past me and land with a resounding thwack against the backboard, all before I’ve even moved my feet. On a third, my racket connects on a Hail Mary, sending the ball coasting into the air, straight up. To his credit, Roddick does what I’ve asked: he shows no mercy; he smashes it.

A few hours later, after stepping behind the bar to try his hand at making one of the U.S. Open’s many signature items, the Grey Goose “Honey Deuce,” Roddick finds me in Mace, an East Village watering hole, and confirms that being smoked was what I’d asked for—yes, I tell him, I really meant it. Ever candid, the former world No. 1 and future father let me pick his brain on all things tennis.

Vanity Fair: How has the American tennis landscape changed since you won the Open in 2003?

Andy Roddick: It’s tough, because I was on the end of the greatest generation ever, from any country. So I think American tennis fans, especially on the men’s side, have been spoiled in the best possible way. I mean, you got Ashe and Stan Smith, into Connors, into McEnroe, into Agassi and Sampras, Courier, Chang . . . it’s just a revolving door of champions.

It’s a long shadow they’ve created. Thankfully for the guys now, my shadow’s a lot shorter than those guys, so they should be fine. [Laughs.] But we have unbelievable talent coming up, from the ages 16 to 19, the best we’ve had in 15 years. It’s the most excited I’ve been about a group of guys in the same age group. In three years, I think the rhetoric will be a lot different around American men’s tennis.

Most memorable match?

Probably the last final against Roger [Federer] in 2009, Wimbledon, for a lot of reasons. It’s the one that I feel like was one of the only matches I played where it was watercooler talk for a week afterwards. Then I went and played D.C. a month later after having not played, and the amount of support I got after that match was different than any time before that in my career. I was the temperamental punk—the this, the that, the young guy, the guy who was throwing rackets, and then, I don’t know what it was. I don’t know if it was being understood a bit more, but the verbiage around me after that match was different than at any point in my career. And I had more fun playing that summer after that match and interacting with people than I did in my entire career.

Let’s talk about what's on everyone’s minds: Serena.

I just love her so much. I grew up with her, from when we’re 8, 9, and 10 years old, so to kind of see what she was when we were kids and now, she’s become this icon. I get goose bumps when I talk about it, but . . . her walk through the shadows of history? If she wins this, if she breaks the all-time Slams record, she’s Jordan of women’s sports. You know, she’s the Jordan of all sports. She’s flirting really hard with being the best woman athlete of all time, and she does it with style. She does it with ferocity. I’m equal parts proud and impressed with her. . . . I will say that I do like that the entire world is paying attention right now. It’s not as if she’s off in some foreign land playing at God knows what hour. The S.I. cover, the New York Magazine cover. I love the way she’s being presented in the media, and the lead up to the U.S. Open. It’s not someone trying to tear her down for antics—I mean, I blew my lid a million times and didn’t get criticized nearly as hard as she ever did or has been—so I like that she’s getting the respect that she deserves now.

There are historical implications. She’s transcending tennis. She’s transcending sports. It’s a pop-culture event mixed with a sporting event mixed with a tennis event. For tennis, it’s a win. For women’s sports, it’s a win. There’s no downside to her winning, and I want to see it.

Related: What Tennis Star Maria Sharapova Thinks About Right Before She Serves