In this R&B/hip-hop jam, Mariah Carey is plagued by thoughts of a past relationship that are keeping her up all night long. Snoop Dogg joins her on the track and tries to coax her out of her funk, saying, "Now you know you look too damn good to be crying."
In her 2020 memoir, The Meaning Of Mariah Carey, the singer said this was inspired by her brief love affair with Derek Jeter of the New York Yankees. "Once, I was feeling intensely melancholy while recalling our short love affair to a friend," she explained. "There was so much energy surging through my body that the champagne glass I was holding completely shattered. I took that intensity and put it in 'Crybaby.'"
This samples the bass line from the song "Piece of My Love
" by the R&B band Guy. Mariah wasn't vibing with any of producer Damizza's suggestions until he played her the 1988 tune. She loved it and immediately envisioned it as a Snoop collaboration, but Damizza had to hustle to get it done in time. "I had to FedEx the track the next day, or it wouldn't make the album. I was like, 'You want me to get Snoop Dogg, get this song together and get mixed, mastered, everything, in one day?'" he recalled to Billboard in 2016
"I called Snoop Dogg, and he was like, 'I got this thing going on and I can't leave the house - you'll have to come to the house to do it.' I was like, 'OK, I guess I'm gonna drive out to Snoop's house.' He had a studio. We got there, and Snoop said, 'This is friggin' amazing, I'm ready let's go in booth."
Damizza, who previously worked with Carey when he remixed her cover of Brenda K. Starr's "I Still Believe," also told Billboard about layering her vocals on "Crybaby." He said: "My favorite thing that Mariah does is to go low, middle and high - it sounds like Bone Thugs-N-Harmony. So I was thinking about the vocals for the song, and I was thinking of 'Breakdown,' and I said, 'Yo, can we do this little thing [layer your vocals]? That's all I'm going to request.' I had left to do the Snoop thing and she layered it herself, just like you hear on the song. We friggin' got it all done, edited everything, and on the next day it was sent.
The song is really about a situation - she literally was walking around on the tippy toes, thinking about an old situation. The thing about her is that her writing is so prolific, but it's so f--king personal. It's really her, and that's what's the f--king scary as s--t."
From her real-life bouts with insomnia to her habit of walking on tip toes, this song paints an authentic picture of the singer. "That whole song is very real," she told Craig Seymour in 1999. "I was going to call it 'Crybaby/Insomniac' and I should have, because that's my theme song. And everybody who knows me laughs when I say, 'I gotta get me some sleep,' 'cause the whole thing is like, 'I don't get no sleep, I'm up all week,' and so they laugh at that because it's very true to life. And even when I say, 'on my tippy toes,' 'cause when I walk around without heels on, 'cause I'm always in heels - even when I was little - I always walked on my tippy toes like this, and I don't know why, but babysitters used to laugh at me, but I always walked like a Barbie, like on my tippy toes, I don't know why, there's really no reason, but I just naturally do that."
This was released as a double A-sided single with "Can't Take That Away (Mariah's Theme)." Billboard changed its rules regarding double-sided singles in 1998 - instead of being credited together on the charts, only the song with the most airplay would receive credit, in this case being "Crybaby," which peaked at #28. Carey was unhappy with the way Sony failed to promote both songs, which only fueled her very public feud with the label. Her subsequent album, Glitter, was released through Virgin Records.
The music video, directed by Sanaa Hamri, opens with Carey struggling to fall asleep. She gets a text message from Snoop Dogg asking what's up, and she tells him about her insomnia. The clip unfolds as she tries several tactics to solve her sleep problem, including taking a bubble bath and eating junk food.