I’ve been saying things like “that’s how I roll” for quite a while now, and it occurred to me to wonder about the history of the phrase. As it happens, there’s a 2013 Stack Exchange post about it; most of the suggested answers are guesswork and contradictory, but there’s one that cites the OED:

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.

So I checked the OED, which does indeed have it as sense VII.36.f.:

intransitive . U.S. slang (originally in the language of rap and hip-hop). To act, behave (in a certain way).…