The realm of hip-hop doesn’t have immunity when it comes to embarrassment. With technology and rap music advancing at the same speed, more cringeworthy moments have been captured over the last two decades via phones, cameras, voice recorders and anything else that you can find in the app store on your iPhone or in the electronics section of Walmart.

Jumping right into a few timely examples, Saweetie went on Instagram Live with Rue21 a few months ago. On the topic of her debut album, the “Tap In” creator was asked who her favorite music artist of all time was, to which she replied that she’d been in her Donna Summer bag. The interviewer followed up by asking Saweetie if she’d like to collaborate with the disco legend and the California native replied that she’d love to. The chances of that are slim considering how Donna Summer has been dead for almost a decade now. The moment was uncomfortable for both her and fans alike.

Awkward moments don’t always come by way of an entire production in an interview. Sometimes they can arise casually and in a funnier light, as is the case with Meek Mill. Back to the swimming pool—this time without fries—Meek tapped into his inner Michael Phelps last week by attempting to dive into a big body of agua at the DreamWorks Water Park in New Jersey. The painful-looking belly flop caused Meek to get cooked by social media. Similar to when his Roc Nation head honcho Jay-Z got caught mid-air a few years ago.

Those two samples barely scratch the surface. Proven throughout the course of history, these moments are bound to occur, especially with such a big spotlight on some of the game’s most popular artists. So with that in mind, XXL takes a look back at 20 uncomfortable hip-hop moments that will make you cringe, laugh or both. Check out the full list below.—Kemet High