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1990-2006 Leo, hands down.
The current Leo is nothing but a middle-aged creep who always bangs chicks under 25. There's rumors that he's seeing some model who was born in 2003. How ****ing creepy is that?
A 19 year old woman and a 48 year old man are both consenting adults, but it's still creepy as hell.
R.I.P. Brittany Murphy (November 10, 1977-December 20, 2009)

Things really started going downhill for him after 2006! Lmao@ the last two

I liked him best in What's Eating Gilbert Grape. He may not have been a heartthrob yet, but his acting was the best he's ever done and he gave Johnny Depp a run for his money.

Good looking
men can get better looking with age.
Most men, like all women, plummet down the ugly tree hard
Alba gu bràth

Men just get better looking as they age so I don't see why not.
My password is password

Do you think he can keep banging under 25s until he croaks?
God willing
Alba gu bràth