The harshest headlines you've seen...

[MisterCreosote]

 

[Donny in his element]

A lot of love for FTU headlines so far.

 

[Songbird]

That is a fantastic breakout box (WRONG SIDE OF HISTORY). That's how you fit a lot of information into a tight little space.

 

[Bronco77]

From the late '90s in the Fort Lauderdale Sun-Sentinel, when the Miami Hurricanes gave up 66 points in a crucial loss to Syracuse, in 120-point, all-caps type:

"ROUT 66"

Rumor had it Butch Davis hated that one.

 

[Liut]

"Waterproof Negro Drowns in Dry Prong"

 

[joe_schmoe]

In the mid 90s when Swtizer was coaching the Cowboys the Cowboys have 4th and 1 and give to Emmit, who is stuffed...twice. (the first play was ruled to have not happen as the two minute warning had been reached).
If I recall correctly the Dallas Morning News headline was "Dumb and Dumber"