Bear in mind that the key factor in the success of insults that sound
like compliments is the delivery. You need to say it sincerely,
smiling, disarming. Let the nature of the insult gradually dawn on the
audience (or the victim).
As you didn't say whether your target is male or female, nor whether
this is a group setting or a one-to-one, nor any other details about
the target, I am supplying a range of general-purpose ambiguous
insults that, if said the right way, will not instantly be recognised
as obvious insults:
"I'm writing an article for the New York Times, and I'd really like to
inverview you. It's about xxx..." (e.g. drunks)
"You're looking great today! I really admire your ..." (e.g. combover)
"You're looking great today! It's amazing what make-up can do."
"Ladies and gentlement, we are honored to have xxx (name) here today.
He has managed to fit us in to his busy schedule, rushing over here
without even having time to change out of his clown suit..."
"I never forget a face, but in your case I'll make an exception."
"Just out of curiosity, are your parents siblings?"
"I'd like to leave you with one thought ... but where would you put it?"
"I'd love to help you out, but I don't know which way you came in."
"You will indeed be fortunate to get xxx (name) to entertain you this afternoon."
"Intelligence and charm has been in xxx's family longer than syphilis."
"I've had a wonderful time, only this wasn't it." (Groucho Marx)
"I worked with xxx on one or two projects ... must have been one, as I
never make the same mistake twice."
"My intelligence (beauty, charm, whatever) is all due to xxx (name). I
must have received his share."
"His face turns heads - and stomachs too".
"I've never had cause to argue/fight/whatever with xxx (name), but if
I did my choice of weapon would be grammar/logic/whatever".
"He enjoyed xxx (e.g. Dickens), and so did the person who explained it to him."
"I remember when that suit was the pinnacle of style."
"Nice outfit/report/whatever. I can really see what you were trying to do."
"Ladies and Gentlemen, doesn't xxx dress well for someone who's color-blind?"
"I believe your family includes two famous boxers ... and a couple of
"Glad you could make it. I heard they were having some problems with
the retirement home bus."
"He carried out every task to his entire satisfaction."
"After his divorce/whatever, I thought he had hit rock-bottom. I was wrong."
"He has the wisdom of youth and the energy of age."
"He has all of the virtues that I dislike." (Churchill)
"A modest person, with much to be modest about." (Churchill)
"He has given me a copy of his latest book. I'll waste no time reading it."
"He has invited me to his graduation ceremony. I'll waste no time getting ready."
"He has Van Gogh's ear for music."
"If he should die, I won't be able to attend his funeral. But I'll
send a letter saying I approve of it."
"You have persuaded me to change my political views. After spending
much time talking to you, I'm now in favor of abortion."
"Keep talking. I always yawn when I'm interested."
"Of all the people I've met, you're certainly one of them."
"That wig hides your lobotomy scar nicely."
"After all, brains aren't everything."
"I heard someone say you are the perfect idiot. I disagree. There's a
little room for improvement still."
"He has a soft heart, and a brain to match."
I trust you will find some potential insults amongst that list. If you
would like to browse some more, try these web pages:
High Class Put Downs
Funny Put Downs
Google Search Strategy: