It was 2001. If you turned on a radio or flipped to MTV, you couldn't escape that distinctive, plucked acoustic guitar riff. Then came the question that defined a generation of R&B: "What would you do if your son was at home, crying all alone on the bedroom floor, 'cause he's hungry?" What Would You Do by City High wasn't just a hit. It was a social commentary wrapped in a melodic hook that managed to be both incredibly catchy and deeply uncomfortable.
Most "socially conscious" songs feel like they're preaching from a mountain top. This one didn't. It felt like a conversation on a porch in a neighborhood most pop stars wouldn't visit.
The Story Behind the Song
City High consisted of Robbie Pardlo, Claudette Ortiz, and Ryan Toby. They weren't just some group thrown together by a label for a quick buck. Ryan Toby, in particular, was already a heavyweight in the industry. You might remember him as the kid with the incredible voice in Sister Act 2: Back in the Habit. By the time City High formed, he was writing for Will Smith and Usher.
The group signed with Wyclef Jean’s Booga Basement label. That Fugees influence is all over the track. It has that raw, live-instrumentation feel that Wyclef championed.
The song actually first appeared on the soundtrack for the Eddie Murphy and Janet Jackson film Nutty Professor II: The Klumps in 2000. It didn't explode immediately. It took a while to percolate. But once it hit the Billboard Hot 100 in 2001, it peaked at number eight and stayed on the charts for nearly thirty weeks. That's a massive run.
Why the Lyrics Caused a Stir
The song is structured as a debate.
The first verse, handled by Robbie Pardlo, takes the perspective of a man judging a woman he sees working at a strip club. He's dismissive. He's judgmental. He asks her why she's "stepping out of line."
Then Claudette Ortiz enters.
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Her response is a masterclass in perspective-shifting. She doesn't apologize. She explains the reality of a single mother with no support system, an absent father, and a child who needs to eat. "For you, this is just a good time," she sings, "but for me, this is what I call life."
It was polarizing. Some listeners saw it as an anthem for empowerment and survival. Others felt it was "ratchet" or glamorized a lifestyle that didn't belong on Top 40 radio. But that tension is exactly why it worked. It forced people to think about poverty, childcare, and the choices—or lack thereof—available to women in the margins.
The Dr. Dre Connection and the Sample
People often forget how much the production carried the message. The track heavily samples "Next Episode" by Dr. Dre, but it's slowed down and stripped back. It takes a "gangsta" anthem and turns it into a soulful folk-hop ballad.
This was a pivot point for R&B. Before this, the late 90s were dominated by "bling-bling" and flashy lifestyle songs. City High went the other way. They went gritty. They went acoustic. They talked about welfare checks and "the man at the liquor store."
The "Life After" for City High
Honestly, the drama behind the scenes was almost as intense as the song itself.
The group only released one album. One. It went Gold, but internal friction tore them apart. There was a messy love triangle between the members—Claudette was initially involved with Robbie, but eventually married Ryan Toby. That’s the kind of behind-the-scenes chaos that ends a group before they can reach their second album.
Claudette Ortiz later appeared on the reality show R&B Divas: Los Angeles, where she spoke candidly about the group's demise and the struggles of being a "one-hit wonder" (though they did have a second minor hit with "Caramel"). She revealed that despite the success of the song, she still faced financial struggles, echoing the very lyrics she sang years prior. It’s a bit of a tragic irony.
Dealing With the Stigma
Even now, people argue about the ethics of the song. Does it exploit the "struggling single mom" trope?
Maybe.
But talk to anyone who grew up in those environments. They'll tell you the song felt like the first time they heard their own lives on the radio. It wasn't "Life" by Des'ree or some abstract concept of struggle. It was specific. It mentioned the rent. It mentioned the lack of milk in the fridge.
The song's legacy is its refusal to offer an easy answer. It doesn't end with the woman getting a corporate job and a white picket fence. It ends with the question. What would you do?
Why It Trends in 2026
You'll see this song pop up on TikTok or Instagram Reels every few months. Usually, it's a younger generation discovering it and being shocked by how blunt the lyrics are. In an era where "hustle culture" is glorified, the song serves as a reminder that for many, the "hustle" isn't about buying a Lambo—it's about basic survival.
The production also holds up surprisingly well. Because it relies on acoustic guitar and soulful vocals rather than dated 2001 synth presets, it doesn't sound "old" in the way some other turn-of-the-century hits do.
Fact-Checking the History
Let's clear up some common misconceptions.
- They weren't a British group. People often confuse them with some of the UK garage acts of the time, but they were straight out of New Jersey.
- Wyclef Jean didn't write the whole thing. While he produced and mentored them, Ryan Toby was a primary songwriter. The man is a pen-smith.
- The song wasn't banned. There’s a persistent myth that it was banned from certain markets. It wasn't. It was just controversial. If anything, the controversy helped it climb the charts.
Actionable Insights for Music History Buffs
If you're looking to dive deeper into this era of music or understand why this specific track resonates, here is how you should approach it:
- Listen to the Self-Titled Album: Don't just stick to the single. Tracks like "The Anthem" and "Caramel" show the group's range. You can see the influence of the Fugees' The Score throughout the entire project.
- Trace the Sample: Go listen to Dr. Dre’s "The Next Episode" and then City High's track back-to-back. Notice how they took a high-energy G-funk beat and turned it into something somber. It's a masterclass in creative sampling.
- Watch the Music Video: It’s a literal interpretation of the lyrics. It uses a cinematic, desaturated color palette that was very popular in early 2000s gritty dramas. It helps put the "story" in a visual context.
- Research the Songwriters: Look up Ryan Toby’s credits. You’ll find he wrote "Caught Up" for Usher and worked with Mary J. Blige. Understanding the pedigree of the writers explains why the song is so structurally sound.
The reality is that What Would You Do by City High remains a benchmark for narrative songwriting in pop music. It proved that you could take a "taboo" subject, put it over a catchy beat, and force the world to look at a reality they usually try to ignore. It isn't just a song; it's a three-minute social experiment that we're still talking about twenty-five years later.