At 28, Melissa Etheridge Was Skinny-Dipping & Partying With Brad Pitt

One of the most electrifying moments in My Window, Melissa Etheridge’s new powerhouse, one-woman Broadway rock musical, comes before she sings “I Want to Come Over.” She tells the audience about sitting in her car outside filmmaker Julie Cypher’s house, willing her would-be lover to leave her then-husband, movie star Lou Diamond Philips, and embark upon their steamy, breathlessly covered affair. (See the situation moodily dramatized by Gwyneth Paltrow, here.)

Etheridge was 28 when she met Cypher, who served as assistant director of the singer-songwriter’s first-ever music video, for “Bring Me Some Water” — the hit single off her self-titled debut album, which she performed at the 1989 Grammys. Their tumultuous relationship and eventual breakup 12 years later inspired songs like “I’m the Only One.”

“I’ve always said that poor choices make great songs,” says the Oscar and Grammy winner, now 62, on a Zoom call from New York. “It’s easy to look back on it now and see I was, in a way, addicted to drama.”

Just a year before, at 27, she’d signed with Island Records after couch-surfing around Los Angeles and building an underground following. Clearly, Missy from Leavenworth, Kansas — whose early teen gigs were in churches, honky-tonks, and penitentiaries — was not in Kansas anymore.

By January 1993, when she decided spur of the moment to come out onstage at Bill Clinton’s inaugural ball, Etheridge’s star wasn’t rising so much as exploding, as were the careers of many of her showbiz friends, like Brad Pitt, Jennifer Aniston, k.d. lang, Rosie O’Donnell, and Ellen DeGeneres. “We were just a lot of kids, coming mostly from the Midwest — Brad was from Missouri — and our dreams were starting to come true,” she says.

After her 1993 album, Yes I Am, sold more than 6 million copies, she entered her “lesbian rat pack era” when, she says, she was the Frank Sinatra to Ellen’s Dean Martin: “We were so famous, it was hard to date. It was weird,” she adds. “For a time there it was me, k.d. lang, Rosie, Ellen. A lot of power there. A lot of interesting stories.” (Their poolside parties in the hills above the Chateau Marmont were so legendary, they inspired Showtime’s The L Word.)

And yet, unlike many young rock stars before her, Etheridge kept her head. “I always felt like I wanted to be genuine in my music, to who I really was. That’s why I came out,” she says. “I didn’t want to join the 27 club. It’s funny because everything started for me at 27. Man, I’m so glad I wasn’t famous in my early 20s. I think insecurity really rules us in our early 20s. We’re all looking for our own character. After 27 is when you really start going, ‘OK, what other people think of me is none of my business. I need to like me.’”

Below, Etheridge talks about her greatest hits, self-preservation in the face of tragedy, and — as a lifelong Kansas City Chiefs fan — Travis Kelce and Taylor Swift.

“It was so much fun. The innocence. Everyone was doing a little bit of work, doing their first things, and we all just believed in Hollywood.”

In your book, Talking to My Angels, you call the period between 1988 and 1995, when you were in your late 20s and early 30s, “these special golden years. We’d eat and smoke and drink and have fun. And we’d end up in the pool with or without clothes on.”

It was so much fun. The innocence. Everyone was doing a little bit of work, doing their first things, and we all just believed in Hollywood. We weren’t unknown. I had an album out, and Ellen was “comedian of the year” or whatever. Megan Mullally was doing little parts here and there before Will & Grace. Once the mid-’90s came, I didn’t see half those people anymore.

But we were just like any 20-somethings. We could eat and drink [and do] a lot more things than we can now. I would love to someday focus in on that time and either do a book or TV show. It was a unique time with people who really crossed all boundaries. We were gay, straight. We were everything, and it didn’t matter.

Do you have private pictures and records from that time?

Not a whole lot. We weren’t taking pictures. We were just hanging out and having fun.

We didn’t self-document and post ourselves back then.

Oh, no. We probably wouldn’t have done half the things we did if we had!

Can you describe the Don’t Ask, Don’t Tell era and being semi-closeted? Was there a fear of being outed?

I was out to my family at 21. I was playing [in] lesbian bars, so every record company that came to see me knew I was gay. To my friends, I was out. There was no closeted-ness there. I wasn’t hiding anything. But it was “don’t ask, don’t tell” in that no one asked me point blank. If you came out, you had to explicitly say “I’m coming out. This is me coming out.”

Which you did at one of Bill Clinton’s inaugural balls.

I didn’t know I was going to do that! Before Yes I Am came out, I was like, “I’m going to come out.” People would change [the pronouns I used]. I would say, “This is written about my lover. They’re…” But I never used gender. And then I read an article where the guy changed everything to “my boyfriend” and “he.” And I was like, “Jesus. People are going to think I’m lying!” That really bugged me. And I’m like, I have to come out. I was prepared. I just didn’t know I was going to do it at the inaugural party. Kind of crazy. But yes, that’s what I did!

You write openly about what we would now call your toxic relationship patterns. And yet, all that romantic turmoil produced some awesome songs.

If someone was mad at me because of jealousy or something, I thought, “Wow, then they must care about me because they’re mad at me.” You know, the way we twist our thinking. I could blame it on my mom and all that stuff from the past, but it’s up to me to break out of those toxic patterns.

But those songs. Oh my gosh. “Come to My Window” was written after a horrible international phone call with my partner at the time, who was back in L.A. and not the most faithful. I hadn’t come out yet, so when I wrote, “I don’t care what they think. I don’t care what they say. What do they know about this love anyway?” — it was sort of me wanting to come out, knowing that was right around the corner, and being defensive about it already.

When you were 11, your choir director told you, “I have to stand you in the back because your voice is so weird.” That didn’t hurt your confidence or make you want to quit singing?

No! It was like, “Oh, I must have a unique voice. OK.” And my mother was like, “Well, if you’re going to do this, then you have to take formal voice lessons.” So I took voice lessons with this opera singer, and after about four or five lessons, she was like, “Missy, you’re gonna sing the way you sing. Tell your mother to save her money.” And again, I didn’t take that as bad. I took that as, “Yeah, I don’t want to sing like this. I want to sing like I sing.”

You were already dreaming of rock stardom?

Oh yeah. Growing up in the ’60s and ’70s wasn’t like now, when everyone is kind of a celebrity. It was just rock stars and movie stars. That was something that only very unique people got to be. And you start thinking, “I don’t know, could I do that?”

You had the confidence to drop out of college and move to L.A. You bet on yourself.

Yeah. I believe in really listening to how you feel and going by that. I believe your inner being knows a lot, and you should go to what feels good.

Do you think people in their late 20s should work as hard as they possibly can to make their dreams come true?

No. I think people in their 20s should understand that happiness is the most important thing. And if working as hard as you can to make your dreams come true makes you happy, yeah. Sure! But if you are not happy doing it, there will not be a happy ending to an unhappy journey.

In 2000, you and Julie famously revealed on the cover of Rolling Stone that your kids’ biological father is David Crosby. The article’s tagline — “The Making of a New American Family” — says it all. You were pushing culture forward as this trailblazing gay icon.

Yeah, yes.

And then when your personal life doesn’t match up with this ideal, there’s dissonance. Can you talk about that pressure?

I mean, you can push culture forward, but it’s not like you have all the answers. There’s no place we get to that’s like “OK, I made it here, now I’m free from worry or stress.” When we broke up, I felt like I’d let the gay community down, you know? But it was my happiness. Nobody knows what was going on inside. I had to let go of all the judgment that I thought was coming at me, or I’d have gone mad. Everyone’s going to have their opinion, but I don’t need to take it in.

I’d like to ask you, respectfully, about the death of your son. [Etheridge and Cypher’s son Beckett died in May of 2020 of an opioid overdose. He was 21.] Is it painful to revisit that loss in the book and on Broadway?

I would not call it painful. If this makes sense, my pain is my choice, and I choose not to be in pain about it. Pain would mean that I think he’s in a bad place or I don’t like where I am. It is very healing, in that every night I get to say “My son would want me to be happy.” Telling myself that is strengthening. I believe that my happiness is important.

That must be comforting to other families in this tragic situation.

Those of us who’ve lost someone to opioid addiction, usually there were a few years of pretty hard behavior. [For] Beckett, it was three years of a slow descent. You get them into rehab, and you hope it sticks. And then it doesn’t, and you don’t know if you should take everything away. You don’t know. There’s no right or wrong to it. And you keep thinking, “Maybe there’s something I can do to change that.” That will torture you. You’re always wondering, “Is this going to be the call?” You always have that sort of dark shadow. When they finally go, it’s like “Well, they’re in a space now of no pain.”

Carrying on with any sort of guilt and shame serves no one. It certainly doesn’t serve me. No one is judging me. That’s probably the biggest part. I’m not saying for the first few days that I didn’t feel incredibly judged by the whole world. Because that’s unfortunately a reaction that people had: “Well, look who their parents are.” That is so hurtful. It’s not easy, but you’ve got to let it go.

In your book, you share emails from Julie after Beckett died. [“Then I got an email from Julie: ‘He’s dead.’ Then another email: ‘And I blame you.’”] Did you clear that with her to include those?

[Shakes her head no.]

That gets to the heart of your greatest fear, that everyone would blame you. I want to hear why you shared that.

I shared it because it was so unkind, and it also showed her level of pain. She had to blame me because it would have destroyed her if she thought anything she did led to his death. I haven’t talked to her since then. I don’t want that. That was the last connection we had. And I do not take it personally. I do not take that on. I do not wish to torture myself. I love myself too much to do that. And I want to be a good mother and a good person for my wife and my other children. I do not blame myself for my son’s death. My son would not want me to blame myself. That’s the thing — I am free to feel that guilt or not, and I choose not to, because it does me and the world no good. There’s no purpose in it.

Despite all you’ve been through, how do you remain kind and open-hearted?

Because of what I’ve been through. Blaming others takes a lot of energy, so I’m just going to put it [toward] myself, and I’m going to find joy in every single thing I do.

On a joyful note, you’re a lifelong Kansas City Chiefs fan. What do you make of all this hoopla around T. Swift and Travis Kelce?

Well, I have two daughters, so on any day the two topics in our household are the Chiefs and Taylor Swift. It was really like my worlds were colliding. I was talking to my oldest, who is 26 — a massive Taylor Swift fan. And she’s like, “OK, well, if she had to be with a football player, I’m glad it’s a Chief.”

I think it’s great for football. I think it’s great for Taylor. I think it’s great for everybody. I think it will bring our nation together.

This interview has been edited and condensed for clarity.

If you or someone you know is seeking help for substance use, call the SAMHSA National Helpline at 1-800-662-HELP(4357).