2020 Jeep Gladiator

As rough and tumble as it gets, the Jeep Gladiator is an undeniable screaming cry for help and attention, and what one drives when one has not outgrown an obsession with legos. It looks like a jeep and a truck were stitched together and that's basically how it drives, too. Its oddball look gets tons of attention on the streets, more so than most luxury rides I've recently tested. It is capable of all kinds of off-the-beaten path feats and reminds everyone that its fun to go outside and play.

The Jeep Gladiator starts at $33,545.