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This was the first hit song from Will Smith which launched his amazing career.
In the first verse he talks about clothes shopping with his mother. His mother insists on buying him outdated styles and off brand clothes. This causes the other kids to make fun of him.
In the second verse he tells a story about the time his parents went on vacation and he stole their brand new Porsche. He picked up a 12 year old girl named Toots and got to second base before getting pulled over and arrested. His parents didn’t seem to understand.
The video is very colorful and the story frolics along to DJ Jazzy Jeff’s upbeat beats.