One Gotta Go: The Biggest Boss — Who Runs It on National Boss Day?

For this week’s One Gotta Go Thursday, we celebrated National Boss Day the only way we know how — by asking the real question: Who’s the biggest boss in the game? The lineup was stacked: Rick Ross and T-Pain’s “The Boss,” Meek Mill’s “I’m a Boss,” Kelis and Slim Thug’s “Bossy (Remix),” and Slim Thug’s “I’m a Boss.” Four heavy-hitting anthems, all screaming confidence, money, and power. But only one could reign supreme.

Let’s start with Rick Ross and T-Pain’s “The Boss.” When that beat drops and T-Pain slides in with “I’m the biggest boss that you’ve seen thus far,” it’s automatic swagger. This 2008 classic helped solidify Rick Ross’s luxury-laced image — think Maybachs, marble floors, and mink coats in Miami heat. It’s one of those tracks that makes you want to fix your posture and check your direct deposit. Then we’ve got Meek Mill’s “I’m a Boss” featuring Rick Ross. This one? Pure hunger. Released in 2011, it’s that come-up anthem — the one you blast when you’re feeling unstoppable. Meek’s energy is unmatched, and Ross co-signing him on the track made it even more iconic. Every bar sounds like a reminder that success isn’t handed out — you’ve gotta take it. Now, I’ll be honest — I wasn’t too familiar with the “Bossy (Remix)” by Kelis and Slim Thug before this segment. I’ve always known the original “Bossy” with Too $hort, but Slim Thug’s verse gives it that H-Town edge we love. It’s smooth, confident, and a reminder that Houston’s always gonna represent when we’re talking boss talk.

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And last but definitely not least — Slim Thug’s “I’m a Boss.” This track dropped back in 2009 and carried that signature Houston sound — slow, laid-back, but commanding. Slim has always embodied what it means to be a southern boss: low-key, respected, and always making money moves. After the votes came in from our listeners, it was official — Slim Thug’s “I’m a Boss” took the crown! H-Town held it down once again, and honestly, it just felt right. On National Boss Day, it’s only fitting that the city’s own boss came out on top.