Rappers like to think of themselves as cool. Hell, they probably actually are. However, that does not mean they always were cool. Unless you were born with the genetic gifts of a child star on a network television show, most of humanity will go through that unfortunate phase when we become living machines built to produce nothing but pure, unleaded awkward. In an increasingly digital age, our embarrassing moments are more likely than ever to be captured on camera. If there is one universal truth is that if you do something embarrassing on camera, our Internet Overlords will find it and put it on the web to our great shame. Rappers are no exception. Earlier this week, a three-year-old video of  a pre-fame Action Bronson in a tampon commercial hit the internet.

Here at XXL, we want you to know that Bronson is not the only rapper that has been caught in a moment that they would like to forget. Thus, we have a compiled a list of rappers before they were famous being caught on video at their most embarrassing moments. Enjoy but nod knowingly at the awkwardness and sympathize. Things get better, guys.


Action Bronson Appears In Tampon Commercial

I suppose there are a worse fates than appearing in a nationally television commercial for women's hygiene products but this doesn't make this particular incident any less hilarious. In a blink-and-you-missed-it moment, Bronson is approached on the street by a frazzled woman asking if he could kindly purchase some tampons for her in the drug store ahead. For a man as verbose as Bronsonlino, Bam Bam's response was hilarious succinct, "What?"

In response this week, Bronson took it it stride tweeting ""I was in a Tampon commercial a couple years back hahaha.... She had just asked me to buy her tampons.... Of course I said yes."

2Pac & Jada Pinkett-Smith Lip-Sync To The Fresh Prince

A little known fact is that Tupac Shakur and Jada Pinkett-Smith attended the prestigious Baltimore School for the Arts together in the late-1980s. In fact, the duo enjoyed a close relationship and were often labeled "best friends" by the people who knew them best. In this gem of a video, we find 'Pac and the future Mrs. Will Smith dancing to her husband's song, "Parents Just Don't Understand," behind a glorious green screen of mall music video kiosk effects.

Jay Z Goes Hawaiian

Before he rocked Tom Ford, he rocked Tommy Bahamas. It took a long time for Jay Z to get on. Before he became the President-texting superstar that we know and love, Jay Z was a struggling rapper-cum-drug dealer associated with his mentor, Jaz-O. In 1989, a flat-topped Jay appeared in  Jaz's video for "Hawaiian Sophie," a cheesed-out novelty song dedicated to Hawaiian women. In the video, we find Jay awkwardly dressing in Hawaiian shirts, being gently lowered on screen via pulleys and awkwardly ad-libbing behind Jaz. I imagine that if he could, Jay would probably spend half of his fortune trying to make this video disappear from human memory. He might be rich enough to fund the technology in the future to make this happen one day.

Prodigy's "Ballerina" Past

It was 2001. Jay Z was making his triumphant appearance at Hot 97's annual Summer Jam concert where he was debuting his newest song, "The Takeover." As the primal thump of The Door's "5 to 1" blared over the speakers, Jay was delivering a historic diss to Mobb Deep when an image flashed upon the screen that would forever change hip-hop. A young Prodigy clad in loafers and white socks high-stepping around in a photo appeared on screen. The crowd snorted derisively at the image and Mobb Deep would never quite be the same after the incident.

Drake Stars On Degrassi

Before Drake was one of the most popular rappers on the planet, he was a simple Canadian television actor in Toronto, starring on the long-running teen soap opera, Degrassi: The Next Generation. Aubrey Graham - as Drake was known then - played the role of wheel chair-bound Jimmy Brooks for seven seasons on the hit show. His most famous moment on the show is when his character an aspiring basketball star was shot by another student in the back paralyzing his character on the show for the rest of its run.

RiFF RaFF Appears On MTV's From G's To Gents

RiFF RaFF might be a walking meme of a human being looking to court as a much attention to himself as humanly possible so it makes a certain amount of sense that he would appear on MTV's make0ver reality show, From G's To Gents in 2008. Jody Highroller appeared as a contestant on the show full of uncouth young men looking to become more gentlemanly than their outward appearances. It appears the makeover didn't take as RiFF remains just as wild-looking as he ever . I imagine in his heart of hearts he would like to have this one back as he looks for people to take him more seriously as an artist.

Game Is Dumped On Change Of Heart

In 2000, a young Game appeared on dating television show, Change Of Heart, with his then-girlfriend. Clad in a unfortunate Hawaiian shirt, Game finds himself being resoundly dumped by his girlfriend on-air after their dates with other people go awry. In a career of often cringe-worthy moments, watching Game get dumped on television remains an awkward experience unmatched by anything he has ever done.