Ne'er-Do-Wells, "Skybolt X-66"
Rock 'n' roll! Straight outta the 50s! Or 1993, whatever.
Don Caballero, "Room Temperature Lounge"
From Singles Breaking Up, Vol. 1, which is a singles comp, as you could probably guess. Kind of hard to believe that you can consider this song and the previous one (separated by a mere four years!) as both being products of the 90s rock underground.
They Might Be Giants, "All Time What"
2015-2018 was an extremely productive period for TMBG, with a flurry of albums driven in part by a revival of the Dial-a-Song project. Of that burst of records, the gem is I Like Fun, a record loaded with catchy tunes, but also some pretty fun song structures. This isn't one of the killer tunes from it, but even as one of the lesser tracks, it still has that big horn arrangement and is a good time.
A pure ripper, this is a delight.
Tommy Guerrero, "Slow Roll"
Tommy Guerrero is both a jazz-funk musician but also a professional skateboarder, so as per official Five Songs policy, we have to hate him. You're not allowed to be good at multiple things around here! Anyway, Road to Nowhere is a pleasant record full of these kinds of jams.