Released: 2002

Features: Kelly Rowland

Yo, grab your 40 and let’s do this. We’re about to break down “Dilemma” by Nelly. This hip-hop classic from back in ’02 is a soul-baring love jam that finds Nelly, the St. Louis rhyme-slinger, caught up in feelings for a woman who’s already spoken for, creating a fierce emotional dilemma.

The track starts with the hook, that catchy melody that has Nelly warbling about being crazy over a woman, even when he’s with his main squeeze. When he refers to his “boo”, he’s using street slang for girlfriend or significant other. The repetition of the phrase “shake it” is Nelly’s rendering of typical club directions, showing he’s caught up in the party life, but can’t shake thoughts of his desired one.

In the first verse, he kicks about meeting an attractive woman who recently moved to his ‘hood and has a thing for him. However, she’s already got a man and a kiddo. When he talks about playing his position like a “shortstop”, that’s Nelly using baseball terminologies to reflect that he’s making moves, ready to nab any opportunity to have her.


The chaser is the second verse where the complexity of the situation unfolds. Nelly’s got this tightrope balance going on. He ain’t about to start throwing blows over a woman, that’s not his style. However, he appreciates this woman’s vibe and style. When he talks about how she “swoops him in his two-seater”, he’s acknowledging she’s also playing the game. She’s got the gangsta edge.

Then you’ve got Kelly Rowland adding the woman’s perspective to the mix, affirming her feelings for Nelly. She’s in it deep, too, man, despite having a man. This love is more than he’ll ever know. This back-and-forth between Nelly and Kelly gives the song its unique tension, that palpable feeling of forbidden love.

And let’s not forget the shout-outs to the regions – East Coast, Down South, West Coast, Midwest – that’s Nelly acknowledging his nationwide fan base. In the early 2000s, region rivalries were real in hip-hop, but Nelly was breaking down barriers, showing love to all coasts and showing that this dilemma transcends regional boundaries.

So to sum it up, “Dilemma” is a dope track that encapsulates the complexity of forbidden love, caught between loyalty and desire, and set against the backdrop of the street life. It’s a hip-hop ballad that takes us deep into the emotional struggles of the urban experience. The dilemma is real, ya’ll.