A list of regrettable font names

Ray Larabie

10: Gyparody
9: Mlurmlry
8: Welfare Brat
7: Sayso Chic
6: Stampoo
5: Relish Gargler
4: Cutiful
3: Mail Ray Stuff
2: Po Beef
1: Huxtable

Beat that!

Craig Eliason

I'd be full of pride rather than regret if I'd come up with Relish Gargler!

Chris Lozos

Bill Cosby loved your number 1 ;-)

Evie S.

As a man with no pride in himself:
• Itis*
• Click Here To View Your Arrest Record Sans*
• Cepok
• Toffson Text*
• Legiblus
• French
• Saberdome
• Unitrow

All regrettable names from my page (except ones marked with *) (shameless plug)
http://fontstruct.com/fontstructors/681805/j4s13

Dave Crossland

https://groups.google.com/d/topic/googlefonts-discuss/3lMdbt8oQ8Q/discussion still amuses me. Good old Adam!

Malcolm Wooden

I always had a problem with "Knobcheese" (if you know what I mean!)

Daniel Goldberg

Monotype Columbus must be mentioned. 

Russell McGorman

Why?

SiDaniels

Hitler Sans, Idi Amin Oblique, Pol Pot Casual