Year: 1988
Produced By: Todd Shaw
Album: Life is...Too Short
Label: Jive

While East Coast rappers were scared to use cusswords on wax, Too $hort was in Oakland stringing together as many as he could—"motherfuck you damn shithead bitch"—eventually taking credit for making the word "bitch" or "beeyatch" as popular as it is today—which, whatever. This is also probably the first instance of a rapper claiming to have received fellatio from the First Lady, while accusing the president of dealing cocaine. Despite being ahead of his time with regard to cussing, $hort still had an old school attitude towards song length. Having the most raps, or being able to rap the longest, was still considered a worthwhile endeavor. At seven minutes forty-five seconds, with no throwaway lines, "Cusswords" is a whale of a song by today's standards.