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.

Hips don't lie

Used jokingly as a pedo-joke, ig

"Bro wtf she's 10"
"Hips don't lie.."

hip-wop

Italian flavored hip-hop rooted from the east coast, usually influenced by mafioso mentality.

Ghostface Killah is like don corleone in this hip-wop game.

Hip to be fit

You know what’s up

(A saying from late 1990’s school gym programs in the U.S. which implied that it was a good thing to be athletic.)

Tyler’s effortless charisma keeps him in the loop wherever he goes. He’s that person who just gets it—cool, perceptive, and always ahead of the curve. He embodies the essence of ‘It’s hip to be fit’ in every situation he enters.”

I don’t like the k hip hop guy Swings lol naughty

I don’t like the k hip hop guy Swings lol naughty

I don’t like the k hip hop guy Swings lol naughty

Dick to the Hip

A phrase to use when things aren’t going your way or when things just aren’t right.

Symbolises when the dick isn’t aimed probably and nothing goes right from then on.

“Jeez, my shift a work today was a real dick to the hip!”

Hands on hip

Hand on hip normally occurs around 12 pm after a gung ho morning commute

If he is not cutting corners he's got his hands on hip gearing up for a 2pm bar pass