If he was on US-60, they basically weren't wrong :P
https://en.wikipedia.org/wiki/Prudhoe_Bay,_Alaska
https://en.wikipedia.org/wiki/Yaviza
Google Maps says it's about a 104-hour drive (without breaks of any kind).
You could also think about borders that are closed. Like if you want to go from Haifa to Beirut, the shortest legal route goes through Jordan and Syria!
Or with the Darien Gap, people asking about how to drive from Panama City to Cartagena might be surprised -- you actually can't get there from there (by road).