Tripper - Daniel LaRusso - Cobra Kai
Grown-up LaRusso's not only still got his sunny disposition (about most things), he REALLY knows his way around cars. Handy to have someone like that along for a long-distance drive.
Tripper - Cisco Ramon - The Flash
Given enough warning about the road-trip, you have to believe that Cisco would have some AWESOME upgrades to make to your transportation. I personally would want him for his music and pop culture trivia alone but the vibing skill could definitely come in handy too.
Rager - Barbara Kean - Gotham
Right, as if Barbara Kean would ever get caught DEAD on a road-trip but let's just (for the fun of it!) imagine what a total disaster that would be. She'd probably: drive like a maniac; blame you for getting lost when she's the one navigating; complain about the car, the weather, the music, and the scenery; and kill someone along the way. Upside: she'd probably insist on really nice hotels and be willing to pay for them herself.
Tripper - Phil Coulson - Agents of S.H.I.E.L.D.
Although Phil would totally be a nice, reliable, dad-fun sort of road-trip buddy, I have to come clean and admit I'm only including him in this list because I WANT TO RIDE IN A FLYING CAR. Seriously.
Tripper - Job - Banshee
Job has had a stressful life. I think a road trip would do him a world of good and knowing that he's a skilled driver (and hacker) with connections to anyone who could possibly be useful across the country, you'd imagine it would be an INTENSELY interesting trip. Just let him pick the music.
Rager - Raylan Givens - Justified
No offense to the good Marshall Givens but the man gets people KILLED. He's a nice guy who's always trying his best at a job he gets done (if not in the prescribed method) but even on his day off, he racks up an impressive body count. I don't know about you but I'd rather not be in the passenger seat when his bullet magnet kicks in.