Continuing the theme from an earlier post about when rap music had only occasional rather than constant name-dropping of expensive brands, what ever happened to carefree and self-deprecating rap songs?
It seems like ever since the crime rate began falling, turning our culture more superficial and based on trivial one-upsmanship, people have been less able to have a good laugh at how bad their life can get sometimes, while still holding out hope that their luck will turn around. (And no, Seinfeld etc. only gave off mock self-deprecation.) The rap world is just a microcosm of the larger trend toward either overly exaggerated bragging about how awesome you are, or else wallowing in self-pity.
It's hard to imagine in the falling-crime era of bragging about your rims and other bling you've used to pimp your ride, but rappers used to have a sense of humor about the less-than-impressive cars they drove. Here's "My Hooptie" by Sir Mix-a-Lot from 1989, three years before "Baby Got Back." That year also saw the popular re-release of "Girls Ain't Nothing But Trouble" by DJ Jazzy Jeff & The Fresh Prince, a lighthearted but not surrendering take on all the crazy shit that girls put guys through. I haven't listened to their first major albums since checking them out from the library over 20 years ago, but I recall a lot of their stuff being goofy like that, much like the Fresh Prince of Bel-Air show on TV.
Since I never got really into rap, I can't remember others off the top of my head, but I'm sure there must be some by the pre-gangsta rappers. The last one that sticks in memory is easily the best:
Positive K, "I Got a Man" (1992)