tragically hip

So hip they are square. The phrase was an insider insult by Fernwood Tonight host Barth Gimbel (Martin Mull) multiple times in the 1970s. Fernwood Tonight was a comedy/parody talk show, an off shoot of another 1970s comedy Mary Hartman Mary Hartman. These Fernwood Tonight episodes where the phrase "tragically hip" is used are on YouTube and also archived at archive.org.

That pork pie hat might only appeal to the tragically hip.