1843 — John S. Robb, "Swallowing an Oyster Alive: A Story of Illinois"
His crop of hair was surmounted by the funnest little seal-skin cap imaginable.
1984, Karl Rohnke, Silver Bullets: A Guide to Initiative Problems, Adventure Games, and Trust Activities
"The simplest are the funnest."
1999, Lorraine Monroe, Nothing’s Impossible: Leadership Lessons from Inside and Outside the Classroom[1]
He found it hard to control his temper, he could be violent without warning or provocation, and yet he could be the funnest person anyone knew.
2004, Trish & Chris Meyer, Creating Motion Graphics with After Effects[2]
This might be the funnest effect added in version 6. It automatically draws lines inside, outside, or straddling the boundaries of a mask shape.
2007, Terry Francona, Pressure on Red Sox as ALCS shifts to Cleveland[3]
That was one of the funnest games I've ever been a part of until the very end, and then it rapidly became a whole lot not of fun. We lost in kind of an ugly fashion at the end.