Definition: (slang) to travel or arrive with a lot of people; to travel with an entourage
Why I Looked It Up
I had heard the term for years. I never quite knew what it meant.
There’s an SNL skit about a rap track that keeps adding guest artists until it becomes unmanageable.
Person 1: New Money Crew roll deep!
Person 2: …yeah, maybe too deep?
I half-wondered if this had anything to do with the Adele song “Rolling in the Deep.” According to this page (which claims an uncited “interview” as its source):
So what does rolling in the deep mean? Adele herself has stated that she adapted the lyric from the expression roll deep. Roll deep (which is used as a verb) has existed since at least the 1990s and has a meaning that could be approximated to having a close personal relationship with one or more people. These people are your ride or die, so to speak. Adele defines this expression as meaning that someone always has your back and you’re never on your own. She says that that’s how she felt in the relationship that the song’s about before that relationship ultimately failed.