title The Upward Way | Episode 10

description Elle’s Playboy cover sends shockwaves through the country, launching Wilder to unimaginable heights—but behind the scenes, the cost of that success begins to surface. As fame spirals out of control, Sylvia reaches a breaking point, and makes a quiet, desperate plea for something more.
Dive deeper into the story and explore upcoming YellaBird productions at: www.yellabird.com
Follow YellaBird Media:
Instagram: @yellabirdmedia
YouTube: YellaBird Media
Theme song: “Everything Changes” by Laura Jane Jones, available on Apple Music and Spotify.
Featuring performances by:
Laura Jane Jones as Sylvia Richardson Robert Fleet as Gentry WilderJanice Lynn Sykes as Roz RichardsonTimothy Stonedancer Coleman as Gordon JenkinsKimberly Conway as Kat Singleton
Rachanee Lumayno - Opening and Closing Narration
Sound design and mixing by YellaBird Media.
Mixing and mastering by Rick Such.
Transcript and additional information available at:
www.yellabird.com

pubDate Wed, 22 Apr 2026 07:07:00 GMT

author YellaBird Media

duration 2105000

transcript

Speaker 1:
[00:00] YellaBird Media presents Higher Grounds, a scripted audio drama written and produced by Kimberly Conway. Higher Grounds contains mature themes and topics that may not be suitable for all audiences. Listener discretion is advised.

Speaker 2:
[00:17] I'm Kat Singleton, and this is Higher Grounds, episode 10, The Upward Way, 1978 to 1980. When Elle's Playboy cover hit newsstands, it caused exactly the kind of stir she predicted. The Monty and Elle comedy hour was canceled within the week. Sponsorships and endorsement deals were pulled, and the two films she'd been in talks for were shelved. The empire Elle's mother had spent years crafting had burned to the ground. And from those ashes, a new Elle emerged, reckless, defiant, but not nearly as free as she hoped to be.

Speaker 3:
[01:44] Alison Andrews, biographer. Elle's Playboy cover was a statement heard all over the world. In the photo, Elle appears to be completely naked, covered only by a strategically placed American flag, draped over her shoulders. She's sitting in a wicker chair by a window, and she has her legs crossed. Ultimately, with the positioning of the flag, you can't see much of anything, nothing but the message she wanted to get across to all the people who had controlled her entire life. The words, not your sweetheart, are painted on her body in black letters. She's looking directly at the camera, her blonde hair must, and the light coming through the window gives it an ethereal glow. Her head is cocked slightly to one side, and her expression is pure defiance. She knows the backlash that's coming her way when the magazine hits newsstands, and she's ready for it. Inside the magazine, there's a full page write up on Wilder's debut album, which dropped the day the magazine came out. And of course, that was a brilliant PR move. They got a huge boost off of the magazine.

Speaker 4:
[02:51] Gordon Jenkins, music producer. We captured lightning in a bottle. Everything hit better than we could have hoped for. Our PR team knocked it out of the park, lining up great press. Of course, we had Playboy in the album release. That was the plan all along. But we had so many other things popping off that we hadn't originally planned on. All of it just kept taking us higher and higher.

Speaker 5:
[03:32] Gentry. Right away, the buzz was more than any of us had imagined. The album was selling out everywhere. The label was scrambling to print more copies. Shows were selling out left and right. I mean, we were off like a rocket.

Speaker 2:
[03:48] Elle and Gentry were on the cover of every tabloid. They had a billboard in Times Square. Their music was playing on every rock and roll station. What seemed like overnight, Wilder became a sensation similar to The Beatles.

Speaker 5:
[04:02] People would get so excited just to see us walking into a venue, they'd cry. They'd reach out and try to touch us as we walked by. It was a trip, man.

Speaker 2:
[04:14] They were adding as many shows to the tour as they possibly could, but it was never enough. As soon as tickets would go on sale, they would sell out, sometimes within a couple of days, most of the time within hours.

Speaker 5:
[04:26] It was a grueling pace we were keeping. It's too much for anybody. You'd get off stage after performing to a sold-out arena. You had so much adrenaline pumping through your veins. You start to wind down somewhere around 4 AM, but then you got a 4 AM radio appearance. It was stuff like that all the time. We weren't sleeping even when we had time to sleep. Naturally, you start looking for some chemical assistance to keep going, you know what I'm saying? People always think I was the one who got Elle hooked on drugs, but the truth of the matter is that it was the other way around. She got deep into it way before I did. Some of that stuff was old hat to her. Her mom had had her on diet pills and speed off and on for years.

Speaker 6:
[05:21] Ros, I was real worried about Elle. It was all so intense, and I didn't know if Elle had anyone she could lean on. Gentry didn't strike me as much of a support system, if I'm being honest. I kept calling, kept leaving messages, but I never heard back from her. I finally caught up with her at the Grammys the following year. I was scheduled to perform with Wilder. I saw Elle at rehearsals, and it was clear then that something wasn't right. She was high as a kite, and I don't even think it was noon yet. That night, 20 minutes before we went on stage, I found her passed out in her dressing room. I don't know how she managed to go out on stage and get through the song, but she did it. After the show, I told her, Elle, you can't keep going like this. She told me she had it all under control. When it was time for us to part ways, I gave her a hug. I kept holding on to her because I just kept feeling like this was the last time I was ever going to see her alive. Gentry came through about that time carrying her suitcases. I stepped in front of him and I said, Get us some help. He said, Yeah, for sure. I didn't bother to say anything else. I knew I was wasting my breath.

Speaker 5:
[07:09] When you spend your whole life feeling like a nobody, and all of a sudden, you got stadiums full of people screaming your name. That's a high you don't want to come down from. I wasn't willing to give that up for anybody or anything. I kept pushing harder and harder, saying yes to every opportunity. Elle was drowning in the water right beside me, and I was too caught up being a rock star to even reach out a hand to keep her afloat. I should have put on the brakes, should have got her some help, but I kept on pushing. You know what they say, hindsight's 2020. I look back now and I see Elle had a lot more skin in the game than I did, literally and figuratively. Wilder was launched off of her reputation, off of her body. I never stopped to think about how much all of it was costing her. I used to think Elle's mom was the worst person around, the way she used Elle, the way she pushed her into show business. I didn't see it at the time, but I might have been worse than Gretchen. No, no. I'm going to admit it. I was worse than Gretchen. Elle jumped out of the frying pan straight into the fire when she married me. It took me 30 years to admit it, but it's the truth. I guess there's nothing like dying to put a man's life into perspective. Knowing your time is about up makes you think about the life you've lived. I see a lot of the mistakes.

Speaker 2:
[08:54] Wait, hold on. Gentry, are you... are you telling me that you're dying? I was with Gentry at his estate working on our third interview when he dropped a bombshell on me. This was weeks before the story went public. The cancer he'd battled more than a decade ago had returned.

Speaker 5:
[09:16] Doctors tell me it's spread. They say there's not much they can do. They can put me on some treatments, try to slow it down, but... It's still gonna take me out. I told them they can keep their chemo. What's the point of living a few extra months if you feel like garbage the whole time you're here? Nah, I'm not going through that again.

Speaker 2:
[09:45] Gentry, I'm so sorry to hear that. I had no idea.

Speaker 5:
[09:51] Nah, what you gonna do? I'm coming to terms with it.

Speaker 2:
[09:58] Gentry got up and walked across the room. He stomped in front of a window that overlooked his property.

Speaker 5:
[10:07] Everything is far as you can see standing near this window. I own it all. The last time I had this place appraised, it was valued at $12.2 million. It's a cruel mistress, you get what I'm saying? You spend your whole life chasing it. Finally you get your hands on it. Get everything you want it. But then you look up and there's nobody to share it with. You screwed over everybody who ever gave a damn about you. And the only people still hanging around are the ones with their hands out. Then the doctors tell you you're dying and what do you got? Nothing that matters, I'll tell you that much. What does it profit a man to gain the world and forfeit his soul? Charles Richardson said that to me once. I think he got it from Shakespeare or the Bible or something. But I have been thinking about that a lot lately. I don't know about my soul. If there's a hell, I made my reservations a long time ago. But I have been thinking, what was it all for? What was all this for? And I don't have the answer. Isn't that something? I don't know. By working on this podcast with you, it's got me thinking. Maybe this is my shot to do something that matters with the time I have left. Maybe this is my chance to make things right.

Speaker 7:
[12:12] Sylvia. I didn't know how to move on from that night in the desert. Didn't know how to process it. I kept reliving every minute, thinking maybe if I had just done one thing differently, I could have changed the outcome.

Speaker 8:
[12:28] I couldn't face Randi.

Speaker 7:
[12:30] She kept calling, kept stopping by the house, but I wouldn't even talk to her. I wanted to, but Randi always had this way of knowing I was lying to her, and she would keep crying until she got the truth. I knew that's what she would do if I let her in, and I couldn't tell her what happened that night in the desert. I couldn't tell anyone. So I kept all that pain inside, and it consumed me. I had terrible nightmares about Tony. I'd see him the way he looked that night in the desert, and I'd wake up in a panic. Then I'd see Carmine lying in bed next to me. It was like going from one nightmare into another. I felt like a prisoner, and I had lost all hope of getting free from him. That's when the drinking got out of hand for me. I was drunk most of the time. I thought I was hiding it well, but Carmine noticed very quickly. He kept asking me to stop. I told him I was fine, told him I had it all under control. And I really thought I did. Until one night, I think this was about two years after Tony died. I was home alone. I put on a record and ran myself a bath.

Speaker 8:
[13:57] And as usual, I was drinking.

Speaker 7:
[14:02] There's a lot about that night I don't remember. But what I do remember is waking up in a puddle of water on the bathroom floor. Carmine was kneeling over me and his clothes were soaking wet. He kept hugging me, saying, Oh, thank God, Marie, I thought I lost you.

Speaker 2:
[14:26] What happened?

Speaker 7:
[14:28] I had gotten too drunk in the bathtub and passed out.

Speaker 2:
[14:33] Was it on purpose? I mean, were you trying to…

Speaker 7:
[14:37] No, no, no, I don't think so. It just happened. Carmine must have come in shortly after I slipped under the water.

Speaker 8:
[14:47] But if he hadn't walked in when he did, I…

Speaker 2:
[14:50] You would have died.

Speaker 8:
[14:52] Yeah.

Speaker 7:
[14:55] Carmine was… He was real shaken up over it.

Speaker 2:
[15:02] Carmine? What about you?

Speaker 7:
[15:06] It's hard to say what I was feeling. It's like that entire period of my life happened to someone else. You know, like, I don't even know that woman.

Speaker 2:
[15:19] You mean, the period after Tony died?

Speaker 8:
[15:23] Yeah.

Speaker 7:
[15:24] After that night in the desert, it was like I didn't exist anymore. There were a few years that I just wasn't there. I don't know how else to explain it.

Speaker 2:
[15:36] What turned things around?

Speaker 8:
[15:39] It was a series of things. I quit drinking and that helped.

Speaker 7:
[15:44] Being able to clearly think again. Carmine threw out all the alcohol in the house after he found me in the bathtub that night. He made it nearly impossible for me to drink. Watched me like a hawk. I knew I had a problem. I knew it was going to kill me. So I got sober with Carmine's help. Then there was the night I ran into Elle at a nightclub in New York. That was another turning point for me. Carmine had some business in New York and while we were in town, he decided he wanted to meet up with some friends at Studio 54.

Speaker 2:
[16:35] Studio 54 was an iconic New York nightclub located in midtown Manhattan. It was a big celebrity hangout, practically impossible to get into. Crowds would gather outside the doors hours in advance, desperate to make it inside. But if you weren't famous or well connected, or if you didn't have the right look, you weren't getting in.

Speaker 7:
[17:06] Of course Carmine had connections. We got right in. We went to the VIP area where his friends were, and I could immediately tell that it was going to be a bad night. Before we even sat down, Carmine got into an argument with a man who he thought was hitting on me. When that finally settled down, Carmine started drinking one right after another. Everyone was passing around cocaine, and he started doing that too. You know, I had never seen him do any sort of drugs before that moment. I don't know what got into him that night. I remember sitting there, stone sober, watching Carmine get more wasted and obnoxious by the second, and I just didn't want to be there. He was getting friendly with this white girl sitting beside him. At one point, I looked over and he was snorting the line off her chest. And I thought, I gotta get out of here. You know, I really wasn't jealous. Carmine meant nothing to me at this point, and he wasn't worth fighting over. But I wasn't gonna sit there while he disrespected me like that. I told him I was going to step outside and get some air. I was almost to the door when I noticed a woman sitting on the floor. She had just gotten sick all over herself.

Speaker 8:
[18:43] There was no one with her, so I stopped to make sure she was all right. I said, hey, are you okay? Do you need some help?

Speaker 7:
[18:53] When she looked up at me, that's when I realized it was Elle. She was out of it, but she recognized me right away.

Speaker 8:
[19:03] She said, Sylvia, I can't believe it's you.

Speaker 7:
[19:08] She reeked of vomit and alcohol. She told me she came with her husband, but they'd gotten into an argument and he left her there. She was in no condition to be left alone. Anything could have happened to her.

Speaker 8:
[19:22] I helped her to her feet and asked where she was staying.

Speaker 7:
[19:25] She couldn't remember, but I was able to piece it together that she was at the Warwick, which was just a couple of blocks away. I thought I could just walk her over and get her to her room, then I could make it back before Carmine notices I'm gone.

Speaker 5:
[19:46] Elle and I got into a big fight at Studio 54. We were coming up on the end of the tour, and our manager said we had an opportunity to extend it for another month. So I told him to go ahead and book the shows. It was a no-brainer. Elle didn't like it. She didn't like that I'd made the decision without consulting her. It all got so out of hand so fast. We both said things we didn't mean. She told me I was just like her mother, that I didn't really care about her. She said I only wanted her for what I could get out of her. It always made me so mad when she compared me to her mother. The truth hurts. Anyway, we blew up at each other. We were two very passionate people. Things escalated quickly between us sometimes. But I was having a good night. I was celebrating. I wasn't going to let her throw a fit and ruin my night. She was creating drama. I said, if you want to be mad, be mad, but do it without me. And I left her there. The guys and I went to another bar.

Speaker 7:
[21:01] When Elle and I got to her room, I helped her into her shower. I gasped when I saw her body. I think I scared her, but I couldn't help it. She said, what's the matter? I said, Elle, you're so thin. I could see every knob on her spine. In those harsh bathroom lights, she looked like death warmed over. Her eyes were sort of sunken in and there were dark circles under them. Her skin was grayish and she had scabs and bruises all over. It was heart breaking. After her hair was washed, I told her to finish up when I made her some coffee. I wanted her to sober up a little more before I left her alone.

Speaker 5:
[21:55] Did I worry about leaving her alone? No, no, not at all. Look, that was our relationship. She did the same kind of thing to me. We always found our way back to the hotel at the end of the night. She was a grown woman. I wasn't her keeper.

Speaker 7:
[22:15] There was a huge suitcase laying open on the bed. So I looked inside to find something for her to put on when she got out of the shower. I pulled out a t-shirt and several loose pills. Fell out, scattered everywhere. I gathered them up as Elle came out of the bathroom. I held the pills in the palm of my hand and I asked her, what are these? She just stood there looking at me with a towel wrapped around her body and her hair dripping wet. Finally, she said, they're my reds. I'll just take them to help me sleep. I said, you don't need any more pills tonight. I wanted to get rid of them, but I thought, what's the point? She could get more with a single phone call, probably have them delivered right to her door. So I tossed them back into the suitcase and closed it. I told her I was ordering room service because I wanted her to get something in her stomach besides pills and alcohol. While we waited for the order to arrive, I combed out her hair and braided it into two French braids, like I had done a hundred times when we were girls. Half an hour later, we were sitting at a little table on the balcony of her suite, eating a full course breakfast. I think it was around 3 a.m. I was so conflicted sitting there with her. I had been away from the club a lot longer than I planned to be. It had been well over an hour at that point. And I was sick thinking about what Carmine would do to me if he realized I was gone. He'd be convinced that I'd gone off with another man, or that I'd tried to leave him. Of course he'd be furious, violent, and there wouldn't be a thing I could do to reason with him. But at the same time, I couldn't leave Elle in the condition she was in. She was coming down hard off of whatever she was on. She wasn't in a good state of mind. She was sullen and emotional. Kept talking about how no one cared about her, and everyone only wanted her around so they could get something from her.

Speaker 8:
[24:26] I was afraid she was going to hurt herself, you know? And I do think she was considering it.

Speaker 7:
[24:33] She kept leaning over the ledge of the balcony talking about how easy it would be to jump. I kept thinking I will never be able to live with myself if I leave, then wake up in the morning to the news that she's dead. So I sat there with her for another hour, watching the clock through the window, getting more anxious every second.

Speaker 8:
[25:02] Finally, I got the idea.

Speaker 7:
[25:05] If I could just get her into bed, if I could just get her to go to sleep, I could get out of there. So we went inside and I turned out all the lights tucked her in like a child. And I sat down on the bed beside her, waiting for her to fall asleep.

Speaker 1:
[25:25] She closed her eyes and a few minutes later, she said, You're a good friend.

Speaker 7:
[25:30] Thank you for taking care of me. She said, Let me come stay with you. I want to get clean.

Speaker 8:
[25:36] I need you to help me get better.

Speaker 7:
[25:39] Of course, I wanted to help her. But I thought, How in the world am I going to help her when I can't even help myself? I was trapped in an abusive relationship with a murderer who controlled my every move. What could I do for her? My hands were tied, so I told her I couldn't help her. And it broke my heart. I remember sitting there in that dark room, tears streaming down my face because I just felt so hopeless, you know? I was trying to be quiet. I didn't want her to know I was crying, but she sat up and wiped my tears. Then she laid her head on my shoulder and said, It's okay. It's all going to be all right. Somehow we started reminiscing about home, about when we were girls, just silly little memories. We started talking about the Divine Darlings and how we all used to sing together. Elle said, What was the one song we used to sing all the time? How did it go? I sang the first few lines. She laid back down, pulled the covers over her. She said, keep singing.

Speaker 8:
[28:21] That was the moment when I truly hit bottom.

Speaker 7:
[28:25] Sitting there that night. My best friend needed me to help her, and I couldn't do it. And I knew I was going to have to face Carmine when I left. I was scared to death thinking about what he'd do, and I just, I felt so defeated. And I realized in that moment that I needed something greater than myself to turn things around for me. I hadn't prayed in years. I wouldn't have even known what to say. But sitting there, singing that old hymn, those lyrics became my prayer. Lord, plant my feet on Higher Ground.

Speaker 5:
[29:36] I went back to Studio 54 just before closing time to see if Elle was still there. Had no sign of her. No one knew where she went. But I did run into Carmine, of all people. Old boy was out of his mind. Ha ha. He didn't know which way was up. He was there by himself, didn't have a dollar left in his wallet. I paid for his cab and helped him get to his hotel room. I never mentioned it to him. He really turned things around for me, getting me that gig on the Monty and Elle comedy hour a few years back. So I figured I could do him a solid without giving him too much hassle about it.

Speaker 7:
[30:27] When I finally left Elle's hotel room, it was after 5 a.m. All the nightclubs were already closed by then, which meant Carmine definitely knew I'd left. I should have been terrified to go back to the hotel and face him. And I was afraid they would get me wrong. But I also had this strange sense of peace. And I knew that whatever happened, it was gonna be all right. When I got to our hotel room, Carmine was passed out on the bed, face down on top of the covers.

Speaker 8:
[31:06] I couldn't believe it.

Speaker 7:
[31:09] Out like a light. So I went and changed into my pajamas and slipped into bed beside him.

Speaker 5:
[31:18] When I got back to my hotel room, Elle was sound asleep. She had even taken a shower, ordered room service. So see what I mean? It wasn't a big deal that I left her behind. She found her way just fine that night.

Speaker 2:
[32:24] Next time, on the season finale.

Speaker 6:
[32:29] Any other time, I probably wouldn't have been so forgiven, but times like that, you just want to hold on to what's precious to you.

Speaker 7:
[32:40] Charles, hello?

Speaker 1:
[32:43] Sylvia, what are you doing here?

Speaker 8:
[32:47] I'm coming home.

Speaker 1:
[33:38] Higher Grounds is a Yellowbird Media Production, written and produced by Kimberly Conway. Sylvia is voiced by Laura Jane Jones. Gentry by Robert Fleet. Roz by Janice Lynn Sykes. Kat by Kimberly Conway. Gordon by Timothy Stonedancer Coleman. Allison by Jennifer Jumas. Opening and closing narration by Rachanee Lumayno. Sound design and mixing by YellaBird Media. Mixing and mastering by Rick Such. The theme song, Everything Changes, by Laura Jane Jones is available now on Apple Music and Spotify. Shows like Higher Grounds are made possible by the support of listeners like you. If you've enjoyed the show, we'd be so grateful if you could take a moment to rate and view us on your favorite podcast platform. Stay connected with Higher Grounds and be the first to know about upcoming YellaBird productions by following us on social media and signing up for our newsletter at www.yellabird.com. Higher Grounds is a work of fiction. Names, characters, places, and incidents are either the product of the author's imagination or used fictitiously. Any resemblance to actual persons, living or dead, events, or locales is purely coincidental. This podcast is intended for entertainment purposes only.