Mariah Carey and Derek Jeter in 1998. Photo from John Barrett (Globe Photos).
By Terrance Turner
Sept. 3, 2020
“It wasn’t raining yet
But it was definitely a little misty on a warm November night
And my heart was pounding
My inner voice resounding
Begging me to turn away
But I just had to see your face
To feel alive…
My apprehension blew away/I only wanted you…“The Roof” (1997), feat. Mobb Deep
To taste my sadness as you kissed me in the dark.
Every time I feel the need
I envision you caressing me
And go back in time
To relive the splendor of you and I
On the rooftop that rainy night.”
With this vivid, evocative prose, singer Mariah Carey recalls a memorable night on the roof, in the rain. She wrote the lyrics to “The Roof” — a dreamy, romantic love song with a hard hip-hop edge — for her 1997 album Butterfly. The album represented a liberation of sorts for Carey; it was released the same year she split from Tommy Mottola, former CEO of Sony Music. (Sony is the parent company of Columbia Records, to which Mariah was signed until 1998.)
In a jaw-dropping interview with Vulture this week, Carey reveals that she wrote the song about New York Yankees baseball legend Derek Jeter.
According to Vulture, Jeter and Carey “met at a dinner party and started text-flirting, secretly, while she was at the end of her marriage to Mottola”. Jeter and Carey shared “a clandestine kiss” on the roof of his apartment building, writes Vulture reporter Allison P. Davis. “There was Moet. She wore a buttery leather Chanel skirt. She remembers her boots and the rain and her hair curling in stunning detail.”
“Of course I do!” Carey told Davis. “I could never forget that moment.” Carey went on to say that “it was a great moment, and it happened in a divine way because it helped me get past living there, in Sing Sing, under those rules and regulations.”
Carey is referring to the $20 million compound that she shared with Mottola. She called it “Sing Sing” — a reference to the famous maximum-security prison in upstate New York. “It was fully staffed with armed guards, security cameras were installed in most rooms, and Tommy was in control,” she writes in her memoir.
Mariah and Mottola married in 1993, when he was 43 and she was 23. They had a lavish wedding, at which luminaries such as Billy Joel, Bruce Springsteen, and Barbra Streisand attended. At the St. Thomas Church in New York, the two married in a grandiose ceremony; Carey’s crème silk gown featured an enormous ball gown skirt and a twenty-seven foot train. She and Mottola flew to Hawaii for their honeymoon. It seemed like a Cinderella story. But the marriage soon went south; Carey reportedly felt trapped in it. “He’s controlling,” a friend of Carey’s told People around the time of the breakup. That matches what Carey herself has said over the years. “It was very controlled,” Carey told Cosmopolitan in 2019. “There was no freedom for me as a human being. It was almost like being a prisoner.”
She elaborates further in excerpts quoted in her book, The Meaning of Mariah Carey: “Every move I made, everywhere I went, I was monitored—minute by minute, day after day, year after year,” she writes. “I was living my dream, but couldn’t leave my house.”
“Even the idea of me doing something he couldn’t control sent him into an irrational tailspin,” Carey writes. She cites an example in which Mottola became livid when an Entertainment Weekly article suggested Carey could co-star in a remake of the 1950 classic “All About Eve”. (The film featured a small but memorable role from Carey’s film idol Marilyn Monroe.) “Tommy read the article and got pissed — at me! Somehow he found a way to blame me for someone else’s fantasy of casting me,” Carey writes. She adds that the gulf between their musical tastes also was a factor: Carey grew up listening to 1980s hip-hop, which was later joined with R&B to create “New Jack Swing”. Mottola disliked hip-hop and felt it was just a passing trend. So Carey’s efforts to incorporate rap into her sound met with stiff resistance.
Carey describes her collaboration with rapper ODB on a remix of her 1995 hit “Fantasy”. She reveled in the song’s new sound, excitedly playing it for her husband and boss. But Mottola balked: “The f–k is that?’ he blurted, according to Mariah. “I can do that. Get the f–k outta here with that.” So the one thing that had brought them together (music) was now a battleground: “Music was our only true bond,” Carey writes in the book, “and now we were light-years apart.”
Eventually, Mottola realized the power of rap as a commercial force and agreed to let his wife collaborate with hip-hop producer Jermaine Dupri. He and Mariah worked on a remix of “Always Be My Baby” (from Carey’s album “Daydream”). The remix involved Atlanta R&b group Xscape and Chicago rapper Da Brat. They all met at Carey and Mottola’s home, which had a state-of-the-art recording studio.
Brat and Mariah were instant friends. “Her energy was irresistible,” Carey writes. “I adored her, instantly.” They had a lot in common: “We were both Aries, both super silly, and both believed in an awesome God.” On the floor of Carey’s shoe closet, she and Brat laughed and talked. They decided to go get French fries from a nearby Burger King. But while the two women enjoyed a joryide in Mariah’s Mercedes, Tommy Mottola was seething — and launching a search operation.
Mottola sent out his security (armed with guns!) to find Mariah. Back at the house, Dupri made frantic calls to Brat: “Tommy is bugging out; he got everybody running around looking for y’all; they got guns and s–t!” While the two women sat in the car eating and cracking jokes, “Jermaine must have called every five minutes, begging us to come back.” Carey remembers that Brat called her out: “You have everything, but if you can’t be free to go to f–king Burger King when you want, you got nothing. You need to get out of there.”
When the two returned, “there were more than ten security personnel standing outside, preparing two large black SUVs to go on a search. They stopped me before I could get up the driveway to the garage, as if I was a fugitive crossing the border,” Carey recalls in her memoir. “While Jermaine was in the studio, concentrating on laying down the beat for the track, security had busted in and interrogated him, with their guns out in broad daylight.”
The situation epitomized Mottola’s control over Carey, which soon became evident to those in the media. A 1996 profile of Mottola in Vanity Fair by writer Robert Sam Anson says: “Mariah’s career was soaring, and Tommy was guiding it every step of the way. He approved her material, oversaw her arrangements, checked her promotion, and, to no one’s surprise, made sure her attorney was Allen Grubman, who, in addition to handling a goodly chunk of Sony’s legal chores, now represented a third of its talent roster and the bulk of its key executives. ‘Allen Grubman is my best friend in the world,’ Tommy says in response to questions about conflicts. ‘End of subject. Over and out’.”
“Mariah, friends say, is a very young 26-year-old. They also portray her as increasingly antsy about her husband’s wardening (‘Always being up my ass,’ a former staff member quotes Mariah as saying), which includes the employment of two bodyguards, whose duties extend to accompanying her to the bathroom door, and the placing on Sony’s payroll of a constant shepherdess, the wife of Epic Pres. Dave Glew.”
Anson continues: “For all of Tommy’s precautions, though, there have been slips: a Concorde flight during which Mariah poured out her problems to Diana Ross; an unwelcome friendship with an old high school boyfriend (‘Tear his eyes out,’ an aide recalls Tommy saying after he saw his wife being ogled, but Tommy says, ‘No, I never said anything like that’) and the most public incident, a noisy quarrel in a Beverly Hills hotel lobby after [the 1996] Grammy Awards.” (Carey had been nominated for a handful of awards, but went home without a single trophy.)
The Vulture profile mentions security cameras in the compound that watched her every move. In the book, she details that surveillance. The Daily Beast notes that Carey describes having to sneak downstairs “for a snack, or to sit at the table and write down some lyrics. But every time, right as I would start to settle into the calm of the quiet dark and begin to find my breath—Beep! Beep! The intercom would go off. I’d jump up, and the words ‘Whatcha doin’?’ would crackle through the speaker.”
Davis also notes that, when they started discussing Mottola during a Zoom call, Carey began to cry. Those tears were a long time coming. In 2008, Carey told Parade magazine: “On my new album [E = MC2], the song “Side Effects” says, ‘Kept my tears inside, ’cause I knew if I started I’d keep crying for the rest of my life.’ It’s really true. At that point in my life, I didn’t cry because I had to be so emotionally cut off to deal with it.”
Sure enough, the lyrics reveal a fraught emotional state that continues to haunt Carey: “Wakin’ up scared some nights still thinkin’ ’bout them violent times/Still a little protective of the people that I let inside/Still a little defensive, thinkin’ folk be tryna run my life/Still a little depressed inside, but I fake a smile/And deal with the side effects.”
Mottola issued a diplomatic statement as Carey’s book neared publication. In it, he wished his ex-wife and her family “the very best”. In his 2013 memoir, Mottola apologized for “any discomfort or pain” he had caused Carey: “If it seemed like I was controlling, I apologize. Was I obsessive? Yes. But that was also part of the reason for her success.” Carey, too, acknowledged to Parade: “I do believe that I learned a lot from him and that he really did believe in my talent and I am very grateful for that.”
By 1996, however, it was clear that the marriage was crumbling. “In the beginning,” Carey writes, “I was walking on eggshells. Then it became a bed of nails, and then a minefield. I never knew when or what would make him blow, and the anxiety was relentless.” She later adds that “everyone around me was connected to Tommy and scared of him. I knew that anything I said would get back to him, and I would suffer his constant rage.”
Into this nightmarish situation stepped Derek Jeter.
The two met at the aforementioned dinner party, at which 20 people were seated around a large dining table crowded by wine and candles. The conversation turned to race, and someone pointed out Jeter’s heritage: “Derek, your mother’s Irish and your dad’s Black, right? Like, so what do you think about all this?” Carey, who also had an Irish mother and Black father, immediately took notice. She looked up; their eyes locked.
“It was if suddenly I could see him,” she writes on page 190 of The Meaning of Mariah Carey. “Derek was definitely no longer pedestrian; he was closer to a Prince Charming.” She continues: “I saw his eyes — enormous twinkling jade pearls floating in a golden-brown pool. It was as if there was no one else in the restaurant or the universe.” The two began talking from across the table. Their shared biracial experience helped Carey realize how alike they were: “Derek was young, mixed, ambitious, and doing his dream job, just like me!”
The two began a clandestine communication, texting and planning times to talk. “While the energy was exciting and romantic, our actual conversations were on the light and banal side. I didn’t care, it was something,” Carey recalls. “Planning and communicating with Derek felt like someone had smuggled a file into my jail cell.”
Carey and Jeter arranged a meeting at a pizza parlor near his apartment. Carey and her assistant told her driver that they wanted to grab dinner. “We’d walk in together, and when Derek came in, we’d give my driver the slip,” she explains. “Derek lived nearby, somewhere we could be private and just chill. My assistant would act as a decoy, and Derek and I would duck out together.”
The plan worked. Carey and Jeter went to his apartment. He asked if she wanted to join him on the roof deck; she agreed. He disappeared and returned with a frosty bottle of Moet. “We went up on his roof, laughed, talked softly, took sips of cold champagne straight to the head, and reveled in our bodies embracing.”
“We whispered a few things, giggled some more and then drifted into the romance of the moment,” Carey writes. “We leaned in, an inch at a time, and melted into a warm, slow, intoxicating kiss. I felt an invisible veil of sadness begin to slip off of me and melt into a puddle at our feet. And in that instant, the sky gave way, and it began to pour. We held on to our kiss; our arms didn’t relax their embrace, and our bodies remained fixed,” she recalls.
“What broke the trance was not the rain but fear again. How long had we been gone? Did Tommy already know? I had to go!” Carey and Jeter dashed back to the pizza parlor, and Carey’s assistant jumped with her into the limo. Once the driver dropped off her assistant, Carey was alone in the backseat of the limo, riding back to Sing Sing. She turned on the radio, and out came the lyrics (and hook) of a hard-edged single by hip-hop group Mobb Deep:
Scared to death, scared to look, they shook
‘Cause ain’t no such things as halfway crooks“Shook Ones, Pt. II,” by Mobb Deep
When she returned home, Carey showered and then got into bed. “Immediately I wanted to go back to the roof and relived the splendor I had just escaped,” she writes in her memoir. “The song I had heard in the car, ‘Shook Ones, Part II,’ by Mobb Deep, started to play loudly in my head, and I began to whisper:
Every time I feel the need“The Roof (Back in Time”)
I envision you caressing me
And go back in time
To relive the splendor of you and I
On the rooftop that rainy night.
The next day, Carey called producers from Trackmasters and got the Mobb Deep sample. She began crafting the lyrics, and the result was “The Roof (Back in Time)”, a vivid depiction of her moment with Jeter. It marked a turning point in Carey’s marriage.
It soon became clear that Mariah Carey was on her way out the door, and Tommy Mottola launched a futile effort to get her to stay. “He bought me a gorgeous but pointless Carnival red convertible Jaguar with a creme leather interior and matching drop top,” she writes.
That car became a sticking point: “One evening I was working with two men I had a significant creative and professional relationship with,” she says, “whose duty it was to have moblike loyalty to Tommy.” Carey was sitting with the three men in the kitchen when Mottola began a rant about the car he’d given her and the estate they’d built together, and how in spite of it all she wanted to leave him.
What happened next was a chilling moment that marked the end of the marriage: “Tommy walked over and picked up the butter knife from the place setting in front of me. He pressed the flat side of it against my right cheek. Every muscle in my face clenched. My entire body locked in place; my lungs stiffened. Tommy held the knife there. His boys watched and didn’t say a word. After what seemed like forever, he slowly dragged the thin, cool strip of metal down my burning face.”
That was the last straw. Carey soon left Sing Sing entirely — and began planning a video for “The Roof”. The romantic moment that had inspired the song occurred in November 1996, just weeks after Jeter’s star-making season with the Yankees.
Jeter spent his entire 20-year career with the New York Yankees. He is the Yankees’ all-time leader in hits, singles, stolen bases, and games played, according to New Jersey newspaper The Record. He won five World Series championships with the Yankees, including one during his rookie season in Oct. 1996 and three consecutive championships from 1998-2000. (The Yankees won again in 2009.)
When he wasn’t playing shortstop and hitting home runs, Jeter was quietly seeing Carey. In December 1997, he showed up on the set of a video that Mariah was shooting — a clue that a romance was already brewing. And “The Roof” wasn’t the only Mariah Carey song inspired by Derek Jeter. In the Vulture profile, Carey revealed that she also wrote “My All” with Jeter in mind. The lyrics outline intense but conflicting feelings: “I am thinking of you / In my sleepless solitude tonight / If it’s wrong to love you / Then my heart just won’t let me be right / ‘Cause I’ve drowned in you / And I won’t pull through / Without you by my side.”
The song was written after a trip the two took to Puerto Rico — which may explain the Spanish guitar and Latin percussion. In an interview with Fred Bronson, Carey explained: “I had gone to Puerto Rico and was influenced by Latin music at that moment. When I came back, the melody was in my head. It was at a melancholy point in my life and the song reflects the yearning that was going on inside of me.” Released in April 1998, “My All” became Mariah’s 13th #1 single.
By then, the romance was public — and in full swing. According to ESPN, Mariah joined Jeter in Florida for his team’s spring training in March 1998. The Yankees began the season 1-4. Tongues began wagging in the sports world, and some blamed Mariah for Jeter’s hitting slump. But the Yankees won 25 of their next 28 games, according to Yankees Magazine. Jeter would eventually earn his first All-Star honor and his second World Series ring. By June, however, he and Carey had fizzled out. Constant media attention was cited as a reason for the breakup.
Still, Carey spoke warmly of Jeter for years afterward. “I think he’s a great guy,” she told Larry King in 2002. “And I really, really love his family. They taught me something special,” she said. “I never saw an interracial family that had stuck together and stuck it out that way. I learned a nice lesson from them.”
Like Mariah Carey, Derek Jeter is biracial. Both grew up encountering racism. Jeter has spoken about being pulled over while driving down the street and being accused of stealing things from stores. Carey’s mother Patricia was disowned by her family for marrying Mariah’s father, Alfred Roy Carey. Carey writes in her book about being invited to a friend’s house in the Hamptons only to be called the N-word. (Comedian Sandra Bernhard reopened those wounds after Butterfly‘s single “Honey” was released, saying during her standup that Carey ‘was acting real ‘niggerish’ up there at the Royalton Hotel suite with Puff Daddy and all the greasy, chain-wearing Black men.’)
Carey speaks explicitly about growing up biracial in the Vulture interview and in her new book, The Meaning of Mariah Carey. The memoir, published by Andy Cohen Books, was released Sept. 29. In the meantime, enjoy one of the songs inspired by Jeter — with a remix featuring rap group Mobb Deep. “The Roof” is embedded below.