
Kevin Connolly reminding me of this
lunatic_banana345 on
Back when Leo was in his early heartthrob days his friends called themselves the āPussy Posseā and Kevin Connelly was part of that crew, as was Lukas Haas, Tobey Maguire, and others.
SignorRoberto on
Name this 70s band
Superpants20 on
Tell Sloan I said whats up
Formal_Chance_4266 on
Sean Penn looks …rough. Oh, and I’m vaguely reminded of Leo’s character in The Departed in this picture (which is a good thing for sure)Ā
Also the manspreading here is genuinely killing me šš
39 Comments
Give my man Leo some shoulder room!
That the lil homie from Entourage?Ā
He looks (clothes, posture) like his character from the departed
https://preview.redd.it/pdmsbbw9ms0h1.jpeg?width=1206&format=pjpg&auto=webp&s=4d68fb265f8c569b0704337739c4be0c75d1b315
This was funny
You really gotta think when Leo is the least problematic person in a given photo.
These seats never look comfortable lol
God Sean Penn looks like shit
Sean Penn has been THROUGH it. Leo looks smushed.
Sometimes I hate being GenX. So much talent, but so many dbags.
Match? Itās a game.
Penn always looks like he just got smacked over the with a two by four
Nightmare blunt rotation
Iām blind asf but Sean looks like the cook from Matilda.
Their ages together equal 168yrs
Their girlfriends ages together probably equal like 65
Use sunscreen
So Sean Penn can show up to a Lakers Game, but he canāt show up to the Oscars?
Who the fuck is Kevin Connolly?
The last pic of Leo reminds of that mario party game where you gotta pinch/stretch Marioās face to make it look like him.
Sorry they don’t real college team to root for.
Someone said Sean Penn looks like his cigar exploded and thatās all I think now when I see him
Yo E, tell Sloan I said what up!
Sean reallyyyyy wants to light a cig. Not infront of athletes only actors lol
Sean Penn looks like if Family Guy did a cutaway gag to a troll doll brought to life that spent 40 years doing doing cocaine
woah the director of GOTTI, sheesh man those two really know auteurs, they must’ve been shitting their pants hoping they got cast in his next movie
Is this the longest amount of time Penn has gone without a smoke?
Yikes
Surprised Sean isnāt smoking a cig on the sideline.
“Do you like Laker Girls?”
All I gotta say is Leo and SP weāre both fucking amazing in One Battleā¦
Kevin Connolly looks like heās there as the DD.
Nothing beats Dillon Brooks courtside hatewatch of Lebron
https://giphy.com/gifs/6Euh0tREmh2BAozZwS
Just for men working hard for Leo.
The Pussy Posse’s still recruiting
Nightmare blunt rotation

Kevin Connolly reminding me of this
Back when Leo was in his early heartthrob days his friends called themselves the āPussy Posseā and Kevin Connelly was part of that crew, as was Lukas Haas, Tobey Maguire, and others.
Name this 70s band
Tell Sloan I said whats up
Sean Penn looks …rough. Oh, and I’m vaguely reminded of Leo’s character in The Departed in this picture (which is a good thing for sure)Ā
Also the manspreading here is genuinely killing me šš