Rollin with a Kennedy got life lookin differently
Dopeass double entendre: When he says Kennedy he means both Dom and the famous Kennedy family (JFK, Bobby Kennedy, etc.).
If you had the chance to roll with the Kennedys at their peak, you were somebody influential/powerful/rich/smart/stylish and so on.
To help improve the meaning of these lyrics, visit "Feelin It/Killin It" by Dom Kennedy (Ft. Skotch Davis) Lyrics and leave a comment on the lyrics box