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 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. Mariah and Mottola married in 1993, when he was 43 and she was 23. 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 the book: “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.” 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.”
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.” Into this oppressive situation stepped Derek Jeter.
The two met at the aforementioned dinner party, and sparks began to fly — inspiring one of Carey’s most memorable singles. “It was a little misty on a warm November night”, she writes on “The Roof”. The accompanying album, Butterfly, was released in Sept. 1997. That would place her clandestine meeting with Jeter ostensibly at Nov. 1996 — just after his star-making rookie 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. “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 Yankees spring training in March 1998. The team 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 being marrying and having children with her father, Alfred. Mariah 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 ni**erish 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, will be released Sept. 29. Until then, enjoy one of the songs inspired by Jeter — with a remix featuring rap group Mobb Deep. “The Roof” is embedded below.