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:
This is their first quotation of the phrase:
The video shows MC Hammer driving a car and some of the lyrics are:
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:
As an aside, the song samples the 1977 Bee Gees hit "Stayin' Alive" and, according to Rap Genius: