It’s happened to every single one of us: we say something that we come to deeply regret later, mainly because we were the ones who made ourselves look so foolish. But luckily for most of us, we don’t record a lot of what we say and then give it to millions of people to analyze and dissect. The 8 rappers here, unfortunately, don’t have the comfort of anonymity to protect them. The following lyrical examples of biting irony are many things: funny, unexpected, enlightening…maybe even those three, and more, all at the same time.

Kanye West — “Out The Game”

Scratchin’ out her maiden and here’s my name

Now I’m sittin’ at the bar with all my guys,

They’re saying, ‘Cheers to you for your future years of pain’ 

Kanye West is the king of irony, and it might just be his huge ego that blinds him to his own personal contradictions. He doesn’t seem to have ever been too troubled by his huge reversal on romance that took place between the Don’s early Freshman Adjustment mixtapes and his marriage to Kim Kardashian in 2014. With a policy flip-flop like that—one right up there with Donald Trump’s—maybe Kanye really could pull off the presidency in 2020.

Lil Wayne — “A Milli”

And I’d rather be pushing flowers

Than to be in the pen sharing showers

In 2009, when Lil Wayne pleaded guilty to criminal possession of a weapon, he certainly did do everything he could to avoid the pen. In fact, his attorney delayed his jail sentencing for a while just so that Wayne could get some dental work done. While we missed his music for a bit, we should also probably be thankful that when he described his daily jail routine in a blog post for his fans, Wayne decided not to use his descriptive powers to depict the Rikers Island shower-sharing scene. 

2pac — “Changes”

I always got to worry ‘bout the payback

Some buck that I roughed up way back

Comin’ back after all these years

Throughout his life, 2Pac always had a well documented forewarning of an early death. This existential angst can be found all over his songs, such as on “How Long Will They Mourn Me?,” when 2Pac relates himself to a dead friend at his funeral. And maybe it was that exact buck from the final verse of “Changes” that came to get him in 1996, when ‘Pac was murdered in Las Vegas in a drive-by shooting. In any event, the answer to 2Pac’s existential question — “How long will they mourn me?” — is this: a very, very, very long time.

Dr. Dre, with N.W.A. — “Express Yourself”

Yo, I don’t smoke weed or cess

‘Cause it’s known to give a brother brain damage

For those unfamiliar with Dr. Dre’s work with N.W.A., these lines might come as a huge surprise. That’s because four years later Dre had done a 180 degree turn in his views on drugs, even naming his first solo project The Chronic. A sampling of a few Dr. Dre song titles since then, like “Kush” or “Let’s Get High” drives this point home. Now we can’t even be sure Dre won’t reverse course again, pull an André 3000 and go completely sober.

50 Cent — “Wanksta”

You go to the dealership, but you never cop nothin’

You been hustlin’ a long time, and you ain’t got nothin’

The only hard thing to do here is choosing which song to use in order to make 50 Cent lyrics take on a whole new meaning in light of his recently declared bankruptcy. That’s because it’s currently Curtis Jackson himself who’s “been hustlin’ a long time”, but now hasn’t “got nothin’.” 50 might regret how he has managed his money, but he also might regret rapping these lines even more.

Eazy-E — “Eazy Duz It”

Well I’m Eazy-E, I got bitches galore

You may have a lot of bitches, but I got much more

Just like the deaths of 2Pac and Notorious B.I.G. warned the rap community and its fans against the danger of petty feuds taken too far, Eazy’s death was a warning sign for his audience against the dangers of unprotected sex. When you consider that Eazy had seven children with six different women, it isn’t too much of a surprise that E found out he had AIDS in 1995. Within a month he was dead, but not before he tried to turn his own tragedy into a catalyst for change: “I would like to turn my own problem into something good that will reach out to all my homeboys and their kin.”

Eminem – “Drug Ballad” 

These drugs are probably going

To catch up sooner or later, but fuck it

Back in 2000 on The Marshall Mathers LP, Slim tried to give his future self a big warning about what could happen to him if he wasn’t careful. It apparently didn’t hit home though, because seven years later Eminem’s excessive drug use was no longer ignorable when he started an intense rehab program. If he had only listened to his own advice, maybe we could have avoided that aptly titled Recovery album, which even Em himself ended up not being too hot on.

Notorious B.I.G. — “You’re Nobody (Til Somebody Kills You)” 

Reminisce on dead friends too

You’re nobody til somebody kills you

With all of his violent episodes and antisocial behavior, 2Pac seemed to have had a definite death wish; perhaps he subconsciously realized that dying was the only way that his poetic messages could live on eternally. But Biggie’s own death, the death of someone full of such honest, bounding life on songs like “Juicy,” seems to have come uninvited. It’s almost as if Biggie had never made this song, then he might have eventually avoided his unfortunate fate. In any event, here we are 18 years later, and music fans everywhere are still sad that these two rap legends’ words eventually came back to haunt their ghosts.