PLAYBOY: What about the marriage part?
McCONAUGHEY: I've seen some great marriages work and some relationships that were great until marriage. I believe in the institution, but I don't feel you have to marry. A kid just needs a mom and a dad. My parents, man—married three times, divorced twice. There's a can't-live-with-you-can't live-without-you statement right there.
PLAYBOY: Do you envy anything about a relationship that would inspire three marriages and two divorces?
McCONAUGHEY: I like the three marriages. I don't like the two divorces; that part I don't envy.
PLAYBOY: Was it awkward running into Tom Cruise when you began dating Penélope Cruz after they split?
McCONAUGHEY: Not at all. In fact, I met him through her. I've run into him since. When a relationship ends, many people feel they have to white out that part of their life. I've never felt like that.
PLAYBOY: You called Sandra Bullock a woman you'll always love. Were you at all heartbroken when she got married?
McCONAUGHEY: No, not at all. That's not how I think. It's not how I loved her or love her.
PLAYBOY: She's not the one who got away?
McCONAUGHEY: No, and I hope she's happy. She deserves to be.
PLAYBOY: Whether because of your romances with movie stars or comparisons made when you first began acting—at least after A Time to Kill—you were called the next Newman and Brando. Did you ever have a difficult time dealing with the attention and the life that came with it?
McCONAUGHEY: Yeah, you go from just trying to get a job, begging to be let into the game and, over one weekend, it's like, boom! When everything started coming in, the most challenging part was saying no. It's not easy today, and it sure as hell wasn't easy at 24. You wonder, Do I deserve all this stuff that's coming at me? But my stock dropped after a few films until about five years ago, when The Wedding Planner worked. Now it's on a real nice level.
PLAYBOY: Did you ever worry that it might all be over?
McCONAUGHEY: I never lost sleep over it, even during a few years when it was hard to find a job. I never thought, My gosh, I'm failing. I always understood the idea of "lean horse, long ride." If you just stay in the game, you'll eventually get the cards you're supposed to be dealt. One thing I did learn is that I'm better when I take risks. I had a year or two early on when I got real conservative in auditions. I'd reach the final callback but never get the job.
PLAYBOY: In what ways were you conservative?
McCONAUGHEY: This was before A Time to Kill, right before Lone Star. I was afraid to look foolish.
PLAYBOY: What changed?
McCONAUGHEY: I got fed up with myself. I thought, You know, you've got to shoot to score, bro.
PLAYBOY: When did you finally do so?
McCONAUGHEY: A Time to Kill, for sure.
PLAYBOY: Initially you were considered for a smaller part in the movie—the role of a redneck.