Learn English – Origin of “how we/I roll”

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The phrase "that's how we roll" (along with variants) seems to have become increasingly popular in recent years. It appears to draw attention to one's behavior or policies, asserting — sometimes ironically — the correctness or importance of them, as in "that's how we do things around here."

How old is this usage and where does it come from?

Best Answer

The OED says it's US slang originally in the language of rap and hip-hop. It's sense VII.36.f. (and sense VII.36.e. is "Let's roll"), under sense VII:

To move or convey on wheels or rollers, and related senses.

This is their first quotation of the phrase:

1991 ‘Hammer’ & F. Pilate (song title), This is the way we roll.

The video shows MC Hammer driving a car and some of the lyrics are:

Down the highway
I'm doing it all my way
Money in my pocket (Yo)
I'll say it feels good
That I got it like that
My top dropped
Her hand is in my lap (my lap)

Alpine kickin' another selection
The girlies keep lookin' in my direction
My tank is full
My fame is strong
I got it like that
So I'm rollin' on...

This is the way we roll
We roll...We roll
This is the way we roll...Rollin'
(Rollin'...Rollin'...I'm rollin' on)
This is the way we roll
We roll...We roll
This is the way we roll...Rollin'
(Rollin'...Rollin'
All through Oaktown I'm rollin' on)

The next quotation is from Puff Daddy's 1997 "Been around World" lyrics.

Searching Subzin.com, the phrase was used in many Hollywood films in the 2000s, but the earliest I found was from a song in 1999's Deuce Bigalow: Male Gigolo: Wyclef Jean's 1997 "We Trying to Stay Alive" (the first single from his debut solo album) and these lines delivered by his cousin Pras:

Well you can tell by the way I roll shorty
that I'm a ladies man, a business man

As an aside, the song samples the 1977 Bee Gees hit "Stayin' Alive" and, according to Rap Genius:

Pras' delivery of these lines is accompanied by a Bee Gees-esque falsetto, and the words and melody are a shout out to the opening of the original “Staying Alive”:

Well, you can tell by the way I use my walk
I’m a woman’s man, no time to talk

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