The old adage says to do this again.
Add one, make a city of fame way back when.
OY becomes IP and you’ll have a nice fall.
Change I to A and you’ll catch it all.
Insert an M: make an invention of Chaplin.
Change T to C and with pain you’ll be grapplin’.
Replace second with H: a winner for sure!
Lose second to last: you’ll want balm for a cure.
Drop the H to make something to go on your head.
Change one and an adage will leave this thing dead.
July 12th, 2011 | Category: 
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try
troy
trip
trap
tramp (I don’t get this bit, it was just the only sensible option)
cramp
champ
chap
cap
argh! Last one I don’t know! x__x
Close enough:
TRY: From the adage “If, at first, you don’t succeed, try, try again.”
TROY: The Greek city which was the site of the Trojan War.
TRIP: and fall.
TRAP: to catch it all.
TRAMP: Charlie Chaplin’s famous character was the tramp.
CRAMP: can be very painful.
CHAMP: a winner!
CHAP: Chapped lips or hands can be cured with a balm
CAP: goes on your head.
CAT: is left dead in the adage “Curiosity killed the cat.”
Great job.