The Number Ones: Jennifer Lopez’s “Ain’t It Funny” (Feat. Ja Rule & Caddillac Tah)


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The first time Ja Rule jumped on a remix of a Jennifer Lopez song — a remix that was really a whole new song — Ja announced himself as loudly as he could: “What’s my motherfuckin’ naaaaaame?” The second time Ja Rule jumped on a remix of a Jennifer Lopez song — a remix that was really a whole new song — he somehow outdid himself. The second time, Ja pushed his raggedy roar into even more extreme territory, and he made his opening line a little bit more specific to Jennifer Lopez: “It! Must! Be! The assssss!” Ja Rule wasn’t good at everything, but he knew how to make an entrance.

“Ain’t It Funny,” the second chart-topping Jennifer Lopez/Ja Rule remix, is a work of pure pop-music formula. A few months earlier, when J.Lo’s single “I’m Real” was failing to make any impact in America, Lopez and her producer Cory Rooney linked up with Ja Rule and his ascendant Murder Inc. label. Murder Inc. producers Irv Gotti and 7 Aurelius threw out the original track and made a whole new one. That “I’m Real” remix became a surprise smash, and it basically forced J.Lo to stop promoting her J.Lo album, since nothing else on the record sounded anything like her one big hit. So Lopez and her collaborators threw together a remix album as quickly as possible, and her second ad hoc Ja Rule collab blew up even bigger than the first. There’s a reason why formulas abound in pop music. Sometimes, they work.

Jennifer Lopez and Cory Rooney wrote the original “Ain’t It Funny” for the soundtrack of The Wedding Planner, the 2001 romantic comedy where Lopez gets with Matthew McConaughey. The song was specifically inspired by a scene in the movie, and it’s all about how love sweeps you up and takes you to unexpected places: “Ain’t it funny how some feelings you just can’t deny/ And you can’t move on even though you try?/ Ain’t it strange when you’re feeling things you shouldn’t feel?/ Oh, I wish this could be real!” The track is built on a clomping club beat and flamenco guitars, and it’s the kind of overblown, romantic quasi-Latin pop that made Enrique Iglesias so famous. Tommy Mottola, Lopez’s label boss, was so excited about “Ain’t It Funny” that he started suggesting songwriting tweaks.

Adam Shankman, the director of The Wedding Planner, rejected “Ain’t It Funny.” In Fred Bronson’s Billboard Book Of Number Ones Hits, Cory Rooney says, “The director felt ‘Ain’t It Funny’ had too much Latin influence for the movie because it had timbales.” Fun fact: J.Lo’s character in The Wedding Planner is named Mary Fiore, and she’s supposed to be Italian. Movies are weird! Lopez’s single “Love Don’t Cost A Thing” showed up in The Wedding Planner instead, and she put “Ain’t It Funny” on her J.Lo album. (“Love Don’t Cost A Thing” peaked at #3. It’s a 5.) Lopez released “Ain’t It Funny” as a single in summer 2001, and she made a sweepingly romantic video with fashion photographer Herb Ritts. The song was a pretty big hit in Europe – #1 in Poland! — but it missed the Hot 100 entirely. Americans wanted something different from Jennifer Lopez.

That original version of “Ain’t It Funny” is a pretty good pop song, and it’s also entirely irrelevant to this column. Other than its title, that song has absolutely nothing to do with the song that eventually topped the Hot 100. Instead, the “Ain’t It Funny” remix had a whole lot more in common with “Always On Time,” the Ja Rule/Ashanti duet that it eventually replaced at #1. At that time, Murder Inc. had an oppressive hold over the pop charts, and the whole J.Lo team knew it. In the Bronson book, Cory Rooney says, “We had changed the sound of Jennifer Lopez [with the ‘I’m Real’ remix], and we didn’t have anything else on the album we could release as a single. We had to do another remix to keep the momentum going.” Naturally, they turned to the same team.

Ja Rule was supposed to write a new song for Jennifer Lopez, but he wasn’t getting anywhere with it. The day that Ja was supposed to be writing that remix, his regular collaborator Ashanti happened to stop by the Murder Inc. studio to pick up a check. She saw Ja lying on the floor, playing video games. (I’ve been around enough rappers to know that Ja was probably playing Madden, but I’d prefer to imagine that Ja Rule didn’t write another #1 Jennifer Lopez hit because he was getting really deep into Ratchet & Clank.) Chris Gotti, Irv’s brother, suggested that Ashanti try writing something, and she came up with all of J.Lo’s lyrics for the remix. Or, again, the “remix.”

The “Ain’t It Funny” remix, like the “I’m Real” remix before it, is its own song. Irv Gotti and 7 Aurelius built a new beat, sampling the deeply funky slow-strut beat from Craig Mack’s 1994 Bad Boy classic “Flava In Ya Ear” — another song where, coincidentally enough, the remix is the definitive version. (“Flava In Ya Ear” peaked at #9. It’s a 10. Because of that sample, Craig Mack and “Flava In Ya Ear” producer Easy Mo Bee got songwriting credits on the “Ain’t It Funny” remix.) Gotti and Aurelius added some playful new chords, making the whole thing lighter and sunnier, and Ashanti wrote a new set of lyrics where the narrator tells off an ex who wants her back. Irv Gotti had to repeatedly reassure P. Diddy, Jennifer Lopez’s ex, that “Ain’t It Funny” wasn’t about him.

Ashanti’s lyrics for the “Ain’t It Funny” remix are simple to the point of banality, but they get the point across. Jennifer Lopez’s narrator has been dumped, and now the guy is coming back, telling her that he misses her, trying to get back into her life. She’s not impressed: “See, it never had to be this way/ You should’ve never played the games you played/ Now I’m seeing that you’re kinda lame, knowing how the situation change.” The guy keeps trying to buy back her affections, but J.Lo reminds him that love don’t cost a thing. (Even a fuck-you song is a branding opportunity.) J.Lo leaves no room for interpretation. Instead, she encourages the guy to “take it as a lesson learned.” But she’s not being nice: “I had enough of being there for you/ Now I’m laughing while you play the fool.”

As with the “I’m Real” remix, Ashanti sang the demo version, and she also sang backup on the remix. But the Jennifer Lopez of “Ain’t It Funny” doesn’t sound like she’s doing an Ashanti impression, the way she does on “I’m Real.” Instead, J.Lo sings the song in her lower register. She never pushes her voice. She’s calm and conversational, which makes her whole unimpressed act hit harder. For me, “Ain’t It Funny” works a whole lot better than “I’m Real,” and that probably has a lot to do with Ashanti, rather than Ja Rule, writing the song itself. When Ja does show up on “Ain’t It Funny,” he’s not really a part of the song. He’s just there for punctuation.

Ja Rule’s verse on “Ain’t It Funny” is limited to a few bars at the beginning of the song. The “must be the ass” bit is fun, and then Ja doesn’t really say anything else. Ja promises to “make you smile in the freakiest manners,” which is a funny little phrase. He also observes that he’s “not Lee Harvey Oswald.” Did anyone ever get Ja Rule confused with Lee Harvey Oswald? What a weird thing to say. Later in the song, Caddillac Tah, a Murder Inc. utility-player rapper, shows up to do some shouting. Caddillac Tah didn’t have Ja Rule’s charisma, and he never made an album or any hits of his own. Instead, he showed up on tracks to do exactly what he does on the “Ain’t It Funny” remix. He would bark out a few bars, sound tough, give everything a tiny bit more momentum, and then disappear. I always liked his voice, and it’s fun to hear this classic mixtape-rapper type yelling about spitting the ism, hitting ’em, and getting rid of ’em on a big pop single.

Ja Rule and Caddillac Tah’s verses don’t have anything to do with Jennifer Lopez breaking up with some asshole. The end of the song doesn’t have anything to do with the rest of the lyrics, either. On that part, Jennifer Lopez and Ja Rule sing a pickup line together: “Baby, is that your girlfriend? I got my boyfriend. Maybe we can be friends. Nana nana nana!” More pop singles should end with couples trying to get a swingers’ orgy going. It’s pretty fun. The rap verses and the end-of-track freakiness shouldn’t really work with the essential breakup-song message, but the whole thing is about Jennifer Lopez projecting mastery and confidence, so it all coheres somehow. You have to be confident to propose a foursome, right?

The “Ain’t It Funny” remix vastly overshadowed the original track. Sweepingly romantic club-pop might’ve still had mass appeal in Europe, but horny, flirty, rap-adjacent R&B had utterly conquered the American charts. Jennifer Lopez had tapped into that sound with the “I’m Real” remix. By the time 2001 ended, the J.Lo album was triple platinum, and Lopez and her team planned out a quickie release for a remix album called J To Tha L–O! The Remixes. (It’s named after one of Ja’s lines from the “Ain’t It Funny” remix.) There are a few club tracks on J To Tha L–O!, as well as one ballad that Lopez and her then-husband, her former backup dancer Chris Judd, wrote for the soundtrack of her abused-wife thriller Enough. But most of the album consists of rap remixes that pair J.Lo with guys like Fat Joe and her ex Diddy.

J To Tha L–O! is a slapdash record, but it honestly makes more sense than the big, centrist Euro-pop of the J.Lo album. Jennifer Lopez grew up in the birthplace of rap music, and she got her start as a Fly Girl on In Living Color. She was always more appealing when she presented herself as a round-the-way-girl rather than a glamor goddess. That’s the version of Jennifer Lopez that we get in the video for the “Ain’t It Funny” remix. Herb Ritts, directing again, films Lopez from the POV of the guy getting dumped. She’s having a big mansion party with all the Murder Inc. guys, with Caddillac Tah apparently recording his verse mid-party, and she doesn’t give a shit about anything this guy has to say. Watching the video, you remember that Jennifer Lopez is more actress than singer, and she has a blast rolling her eyes and projecting her annoyance. She knows that she’s one of the most desirable people in the planet, and she relishes the opportunity to let this dummy know. She looks magnificent, obviously. You can see why Diddy, watching this video, might feel a little ego-bruised.

The whole Murder Inc. makeover worked wonders for Jennifer Lopez. At the time, her movie career wasn’t exactly at its peak. (Her two 2002 movies were Enough and Maid In Manhattan — not her best work. Rougher days were coming.) But those Murder Inc. remixes presented her as someone who was conversant in rap, which was becoming the dominant language of the pop charts. She followed the “Ain’t It Funny” remix with another remix single, the Trackmasters’ take on her song “I’m Gonna Be Alright.” The remix was supposed to feature 50 Cent, who was signed to the Trackmasters’ imprint at the time and who will eventually appear in this column. 50 had recorded a verse for the remix, but 50 didn’t get along with the Murder Inc. guys, and he believes that they lobbied to have him removed from the track. Instead, Nas showed up on the “I’m Gonna Be Alright” remix, and the song peaked at #10. (It’s a 7. Nas’ highest-charting single, 2003’s “I Can,” peaked at #12.) Jennifer Lopez stayed in that lane, and she’ll be in this column again, alongside a different Queens rapper.

But we won’t see Ja Rule in this column again. Ja Rule and Murder Inc. were a flame that burned fast and bright on the pop charts. They were not built to last. Ja kept making hits for a few more years, but the moment when “Always On Time” and “Ain’t It Funny” went back-to-back at #1 was unquestionably Ja’s peak. This wasn’t just a case of the public getting sick of a particular sound. Ja and Murder Inc. had serious issues. They had problems with their friends, and they had problems with their enemies.

Ja Rule and Irv Gotti came from the Hollis, Queens, which had been a quiet lower middle-class neighborhood before the crack epidemic of the ’80s. When crack hit, that part of Queens served as the home base of a few notorious homicidal drug-dealing crews, and the leader of those crews became local celebrities. One of them was the Supreme Team, led by Kenneth “Supreme” McGriff. Members of the Supreme Team were implicated in a whole lot of murders. Ja Rule and especially Irv Gotti weren’t street guys. They were indoor kids who mostly worked on music in basements, aspiring to the success of Queens rap groups like Run-DMC and Onyx. In 1994, Ja Rule’s pre-fame group Cash Money Click shot the video for their song “Get Tha Fortune” outside of Supreme’s old territory, and Irv was shocked when he learned that Supreme, who’d just finished an eight-year prison term, wanted to meet him.

By all accounts, Irv Gotti and Ja Rule were utterly starstruck by Supreme, and Supreme hovered around Murder Inc.’s operations for a long time. The Murder Inc. guys became pop stars without any criminal assistance, but they loved the idea of the street credibility that Supreme’s presence gave them. When Ja Rule got his chain snatched in Queens, he turned to Supreme to help him get it back. Irv helped Supreme get financing for Crime Partners, his straight-to-video movie adaptation of a Donald Goines novel that he’d read in prison. At the same time, Supreme was still active in the underworld, and bodies were piling up around him. Late in 2002, Supreme was arrested on a gun charge. A few weeks later, the FBI raided the Murder Inc. offices. Eventually, feds charged Irv and Chris Gotti with laundering Supreme’s money. The two brothers pleaded not guilty. They were looking at 20 years in prison, and they fought the case.

The Gotti brothers’ trial happened in 2005, a few months after I moved to New York and started working at the Village Voice. One of the paper’s editors suggested that I cover the trial. I had no idea what I was doing. I’m not a trained journalist, and I’d never even been in court for anything other than my own traffic fuckups. But I did it. I was in that courtroom every day, and I’m glad I was. It was a complete media circus, and I was part of it. The whole spectacle was fascinating and boring at the same time. Celebrity guests paraded in and out — not to testify, but to watch and to support the Gottis. Ja Rule was there every day. Dame Dash was there a lot. Fat Joe. Russell Simmons. The day that Jay-Z walked into the courtroom, there was an audible gasp, and the normally-unflappable prosecutor tripped over her words for just a second.

I didn’t know this at the time, but federal prosecutors almost always get convictions. This time, they did not. The Gottis had very expensive lawyers, two total showmen who seemed to delight in tearing up the evidence, and the feds’ case seemed pretty flimsy to me. I truthfully have no idea whether the Gottis helped launder Supreme’s money, but the prosecutors didn’t convince me. After two weeks, the jury found the Gotti brothers not guilty. Somehow, after the verdict, I ended up in an elevator with the Gotti brothers and Ja Rule. In my memory, it was just those guys, their lawyers, and me. They were jumping up and down, screaming in triumph. I watched Ja Rule running through the court’s hallways, yelling, “It’s Murda!” That was a good day.

But Murder Inc. had another big problem, one that coincided almost exactly with the feds’ investigation and prosecution. 50 Cent came from a nearby Queens neighborhood, and while Murder Inc. flourished, 50 struggled. He was signed to Columbia, but he couldn’t get his music released. 50 has a more serious criminal background than Ja Rule, and he wasn’t too happy about Ja’s success. 50 also had a habit of naming names — not just those of his perceived rap rivals but those of the Queens street figures that had been around when he was growing up. One of those street figures was Supreme, who did not appreciate hearing his name in 50’s music. 50 was also clowning Ja Rule directly as far back as the 2000 mixtape track “Life’s On The Line.”

50 Cent and Murder Inc. weren’t just going after each other on record. A couple of times, 50 got into studio brawls with the Murder Inc. guys. In one of those fights, 50 was stabbed. More stuff happened. We’ll discuss 50’s whole eventful rise when this column gets to him, but short version: 50 got shot nine times and survived. Columbia dropped him. Instead of licking his wounds, 50 hit the street with an instantly legendary mixtape run that included a great many songs attacking Ja Rule and Murder Inc. Soon enough, Eminem and Dr. Dre signed 50 to Shady and Aftermath, and 50 became one of the biggest stars in rap history almost overnight. 50’s first hit, the 2002 track “Wanksta,” is entirely about Ja Rule, and it peaked at #13.

While 50 was on the rise, Ja Rule was still making hits; he got to #2 with the 2003 Ashanti duet “Mesmerize.” (It’s a 6.) But Ja’s whole act almost immediately seemed soft and tired. 50 Cent was the underdog, and he just obliterated Ja. Ja and Murder Inc. responded by taking shots at 50 and everyone associated with 50 — Dr. Dre, Busta Rhymes, Eminem. Eminem, an artist who will soon appear in this column, did not appreciate what Ja had to say about his daughter, and he retaliated hard.

A few years after those final hits, Ja Rule was off of the Def Jam roster, and his career was effectively over. Ja kept releasing music, but it didn’t catch on, and his life fell apart in other ways. He spent a couple of years in prison on gun an tax evasion charges. Various comeback attempts didn’t pan out. Ja showed up on a couple of bummy reality shows, and he served as one of the co-promoters of 2017’s Fyre Festival, a hilarious con-job boondoggle that resulted in one of the most giddily fun internet days that I can remember. Later, two different streaming services commissioned schadenfreude-rich documentaries about the Fyre Fest. The Fyre Fest situation wasn’t Ja Rule’s fault, and he’s not the guy who went to prison soon afterwards. But Ja Rule had been spinning his wheels for years, trying to do anything that’ll earn him some money or return him to the spotlight. Five years later, that’s still what Ja’s doing.

We won’t see Ja Rule in this column again. I guess it’s possible that Ja Rule could stage a comeback, but come on. That’s not happening. We will see Murder Inc. one more time, and that will happen very soon. And we’ll see a whole lot more singing rappers. Ja Rule didn’t invent the singing-rapper archetype, but he used it to briefly become a dominant force on the pop charts, which nobody had ever done before. Ja Rule’s run didn’t last, but the singing-rapper archetype sure did.

GRADE: 7/10 - The Number Ones: Jennifer Lopez’s “Ain’t It Funny” (Feat. Ja Rule & Caddillac Tah) (

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