What does the word "rakish" mean to you?

Don’t bother looking it up. I know what the dictionary says it means. I’m just curious what you think it means.

I imagine a dirty old man. Like Jack Lemmon’s dad from “Grumpy Old Men” (Burgess Meredith?).

“What Rakish Means to Me”
An Essay by delphica

Ok, it’s not really an essay. But I use rakish to mean a man who has a sophisticated, almost dangerous, international playboy type attitude, but is in fact a teddy bear underneath. I think it’s one of those words that sometimes means almost its opposite – an actual rake would be a cad, but someone who is rakish is only acting like a rake, but really has a heart of gold.

For some reason, the first thing that came to mind was Jason Priestly – I always feel like someone in Hollywood believes Jason Priestly comes across as rakish, while in fact he is only goofy. How odd that I can only think of an example of someone who is not rakish to illustrate my meaning.

For some reason, the only thing I associate with “rakish” is “angle of hat.”

I think it means “rough” or “scratchy”.

Ooooh, I always think of a dashing, devil-may-care, slightly naughty young man. Pre-World War II, of course. I can’t think of any lovely modern rakish men.

Errol Flynn.
Montgomery Clift.
(maybe) Johnny Depp.

Rakish- Dashing, devil-may-care, reckless, charming with an air of drama & danger.

A handsome pirate.

A combination of ‘suave’ and ‘womanizing’

I’m with racinchikki. Setting my fedora to rakish angle as we speak.

I’m with amarinth on this one. I also think a rakish man couldn’t be short for some reason.

Rakish: cocky and handsome, with a perpetual smirk; devestatingly charming. i.e Rhett Butler or the Dread Pirate Roberts.

Thin and sleek.
I don’t know why.
And it only applies to men, in my mind.

Like ShibbOleth, I think Errol Flynn personifies the word. Dashing, slightly wicked, debonair, and very successful with women.

Heh.

Dashing. The angle of the hat gives a wicked-twinkle-in-the-eye persona to the whole person. Think Terry Thomas meets Dirk Bogarde.

Clark Gable as Rhett Butler.
Rakish is sexxay.

Ukulele Ike. Manhattan. Cajun Man. Dr. Matrix.

Sexy and handsome in a rather dangerous, untrustworthy playboy sort of way. Slightly old-fashioned, but dashing nonetheless. A very white and even-teethed grin. Dark hair and glittering eyes.