Define Rolling Deep Meaning

Rolling Deep
Going out with several people, greater than 2. The term is used as a verb and accompanied with the number of people you are with.

Dude, we are rolling deep tonight.
By Zola
Rolling Deep
means when you are going out, playing out as some call it.

James:you rolling deep tommorow

Grayham: im already rolling deep with Becky, you can tag along too if you want?
By Lotti
Rolling Deep
When a group of friends get together in search of girls. It may be a place, like the mall, park, etc.

Yesterday we went rolling deep, but Lucas likes guys, so he was not rolling deep.
Edder brought some girls from the mall, he is rolling deep.
Sergio and Rene are talking to the hot girls, they are rolling deep.
By Cherida
Roll Deep
To go anywhere with a large group of people. People will mean mug and want to fight you, but will not due simply to the size of your entourage

Safety in numbers

By Scarlett
Roll Deep
Rolling Deep

With all the dangers and precarious situations the modern hax0r can find himself in on the streets, the ninties have brought forth the need to "roll deep." The whole rationale behind the concept of rolling deep lies in the age old adage. "Strength in numbers," or something along those lines, although rolling deep by no means requires a large group or backup posse. The term rolling deep stems directly from the world of hardcore hip hop and gangsta rap, and is often used in conjunction with phrases like, "Ya best proteck ya neck," "bakdafukup," or other equally street-smart phrases that manage to incorporate both defensivness and threat. In any case, the implications are easily identifiable and the prmoise of quick retaliation looms in the foreground; rolling deep is a means of letting people know that you are not to be fucked with. The perils of being caught slippin' in this day and age are just too great. I know the value of rolling deep and have integrated it into my daily routine, rolling deep for such mundane tasks as getting a late- night snack from the fridge, buying a new sweater, or making a important phone call home. Hopefully some of the following tips, examples, and observations will acquaint you with the ways of rolling deep as fuck, 'cause it's too dangerous to be caught shallow.

Put on the hardest clothes you can find (consult the latest number one video on Rap City) and practice scowling in the mirror for a few hours. The scowl is on the most integral aspects of rolling deep and must be perfected, although allowances can be made for the Flava-Flav type joker in every roup. Take a deep breath and tell yourself you are hard until you believe it.
Pretend you are in a rap video, running down the street in slow motion or backing up the MC. Visualize yourself as an actual member of a video posse.
Practice the "What the fuck?!" arm gesture (both arms open, palms spread outward) until it becomes an automatic response to any question, especially if from a parent, cop, boss, or teacher.
Grow some sort of "hard" facial hair.
Wear a very unhip pair of sunglasses--not bullshit Oakley or Arnet, but something like cop glasses or oversized mom-style glaasses. Basically anything you can snag out of a lost-and-found-bin will do.
Look around a lot, like you expecting static from any direction.
Cultivate a fake limp or strut and walk extremely slowly.
Refer to people only as "bitches" or "fools." Learn to integrate the following words or phrases into your everyday speech, regardless of their meaning in your life: gat, nine, blast in the face, bitchslap, gangstalean, etc.
You are now ready to assemble the crew and synchronize the eight-step rolling deep program. Usually a larger group will signify a deeper roll, but this is not always the case. Certain people will never attain the ability to roll deep, no matter how much backup they have. Conversely, some motherfuckers roll deep when hanging out on solo tip. Some of the deepest rollers are the strong, silent types who can handles themselves in any situation. Consider the following list of some people who roll deep and some who don't quite make it.

Deep As Fuck:

Wu-Tang, the Warriors (from that old '70s movie), this dude I once saw lounging in a designer sweatsuit and shades, Slayer.

Wading Pool:

Hammer, New Kids On The Block, Blackstreet, any fast food employee or manager, rock star snowboarders, bitch-ass rollerbladers.

Of course those you new to the ways of rolling deep should never try to bust a flex on someone with experience. First things first, you should go in gradually, the way one would enter a pool of freezing water. You should initially roll deep only on inanimate objects such as street signs, a jammed or locked door, or a soda machine that shorted your coin. From that point you should work your way up to blind people or alley cats, but only when you feel comfortable. Progression will naturally lead you to flexin' on old ladies and infants. Get confident, live your lyrics, and work your way up to speed. Eventually you'll be able to walk the streets with pride and conviction that can only come with the knowledge that your are rolling deep.

We roll 6 or 7 deep wherever we go
By Vivianne
Rolling Deep
When a group of poople are walking or chilling together. Usually described for gang members. When people are rolling deep YOU DO NOT MESS WIT EM OR YOU WILL GET YOUR ASS BEAT.

Hater1: I thought you said you were gonna jump the Prince. I knew you were full of it.
Hater2: Nah i came with my clique but they punked out when they saw his crew.
Hater1: WHy? He was rolling deep?
Hater 2: Hell yea! at least 15 of em kats. We couldnt get near um.
Hater1: You pussy.
By Krystal
Roll Deep
Going somewhere with a large amount of people.

By Janet
Roll Deep
When you go somewhere with a lot a people.

By Siusan
Roll Deep
to have a big group of people, i.e. an entourage

"damn homeboy is rollin twenty deep" means to have an entourage of twenty people
By Alameda
Roll Deep
V. The combination of 'rolling', which refers to movement, and 'deep', which refers to 'many'. In lay, this would refer to one, or more than one, dominant male being led with a posse there for the sole purpose of protection, reputation, or intimidation.

Man A: You comin' to the club later?
Man B: Hell yeah, we finna roll deep in that.
By Dion