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Matthew Perry On 'The Daily Show': Masturbating Into Money, Setting Up Jennifer Aniston On A Date With Jon Stewart (VIDEO)

First Posted: 02/03/11 12:04 PM ET Updated: 05/25/11 07:30 PM ET

Maybe if Matthew Perry had a better idea how to spend his money, he might be a little bit happier...

Perry joined Jon Stewart on 'The Daily Show' on Wednesday to discuss his new show, 'Mr. Sunshine,' and, well, talk about how his life isn't so sunny. Or, at least his demeanor isn't.

Talking about a character based on his best friend, Mark Holder, whom he calls "an impossibly happy guy," Perry said that when Holder gives him his happy status updates, he tells him, "terrific, I'm going to go masturbate into some money."

Later on, Perry brought up a moment from his and Stewart's past -- Perry appeared years ago on Stewart's first talk show -- and remembered that Stewart once asked him to set him up on a date with Jennifer Aniston. Couldn't get it done, he said -- because he couldn't even get a date with Aniston himself.

Turns out, Stewart did it himself -- he and Aniston went on a group dinner date, which they laughed about back in August.

WATCH:

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Maybe if Matthew Perry had a better idea how to spend his money, he might be a little bit happier... Perry joined Jon Stewart on 'The Daily Show' on Wednesday to discuss his new show, 'Mr. Sunshine,'...
Maybe if Matthew Perry had a better idea how to spend his money, he might be a little bit happier... Perry joined Jon Stewart on 'The Daily Show' on Wednesday to discuss his new show, 'Mr. Sunshine,'...
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HUFFPOST SUPER USER
dbrett480
02:04 PM on 02/05/2011
His new show looks terrible. I bet it won't make it past 12 episodes.
04:52 PM on 02/04/2011
What a non-story --- nothing particularly interesting here, IMO. And I like Matthew Perry!
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wegroove
07:11 PM on 02/06/2011
he was funny on stewart and his show seems to be promising. I wish Mr Sunshine was on NBC or CBS and that it was on same timeslot as cougar town. We would have had a competition between Courtney and Matthew or Mattney Chandler and Monica or mondler
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HUFFPOST SUPER USER
Said One
09:12 PM on 02/03/2011
Also I want Mathew Perry I always found him to be very sexy
HUFFPOST SUPER USER
wegroove
07:06 PM on 02/06/2011
u want him? like what, u imagine u're monica and he's chandler? LOL
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HUFFPOST COMMUNITY MODERATOR
Craig 212
Tide goes in, tide goes out.
08:08 PM on 02/03/2011
I've always liked Matthew Perry, and I hope his new show does well. It looked funny in the clips I've seen of it, but I'm just not sure I like the premise. A sporting arena? That's not really my cup of tea.
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KellyRyan
A micro-bio for one who has none.
06:06 PM on 02/03/2011
TMI
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vaf112675
Read my comments. You'll know me by them.
04:51 PM on 02/03/2011
He was the funniest one in Friends. Hope this new show does ok.
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justoverit333
make art not war
03:55 PM on 02/03/2011
I like Matt. Hope the show does well.
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wegroove
03:47 PM on 02/03/2011
he might be the least talented, but his character remains the most popular of the show...

I'm just sayin!
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HUFFPOST COMMUNITY MODERATOR
Craig 212
Tide goes in, tide goes out.
08:06 PM on 02/03/2011
Chandler was always my favorite character, and I don't think he's the least talented at all. That would probably be David Schwimmer.
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wegroove
07:07 PM on 02/06/2011
i would say leblanc and anniston were the least talented...
03:21 PM on 02/03/2011
I don't think that any of the 6 from "Friends" was a very good actor. I don't think they were picked on the basis of how good they were, but rather on what they looked like. I always thought that Jennifer Aniston was the LEAST talented of all 6 though. She just doesn't act very well. I have seen excerpts from some of her movies too and, well. . . . . . . .BLECH!!!! She is simply a pretty face who can't act her way out of a paper bag. The powers that be keep putting her in these stupid lightweight comedies and they all bomb at the box office. When are they going to get the hint that she was at her peak of performance as a sitcom person.
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Said One
09:11 PM on 02/03/2011
She acts brilliantly and delivered a lot of the punch lines and all of them were very good at comedy which is hard to do
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wegroove
07:08 PM on 02/06/2011
Mr Punchline on friends and they all have always admitted it, was Perry, period and the most naturally funny guy of the 6 was Perry, they all have said that, he doesn't need a script to be funny!
04:55 PM on 02/04/2011
Sorry, but I thought Aniston was an excellent comic actress with terrific timing. IMO, all were great in their respective roles and it was a great ensemble cast. I know people liked Seinfeld for the ensemble, but I liked "Friends" better because the characters (for me, anyway) were more likeable & endearing.
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FTracy3
My micro-bio is as empty as the rest of my life.
02:07 PM on 02/03/2011
Not at the same time, I hope. That would be creepy.
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roch20
"What you see is what you get"
01:42 PM on 02/03/2011
I like Matt, he's fine! Back off haters!
06:51 PM on 02/03/2011
Don't expect the "haters" to even have a clue about backing off. It's what they do and all they know how to do. Requires no intelligence. NO tact. No nothin'.

It is to pity them.
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HUFFPOST SUPER USER
roch20
"What you see is what you get"
01:40 PM on 02/04/2011
Couldn;t agree more, @sedum13; too bad, thou!
01:11 PM on 02/03/2011
The least talented of the group, the new show looks horrible and his bit on Stewart was as funny as root canal.
01:21 PM on 02/03/2011
Ugh, I don't know, David Schwimmer got SO annoying for the last....8 seasons or so. And I used to think that Lisa Kudrow was talented until I realized that every character she plays is basiclly a different degree of Phoebe.
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HUFFPOST COMMUNITY MODERATOR
J0E1
Phil Hill 2012
01:37 PM on 02/03/2011
The dentist has to lock my jaw open when he does my root canals because I just can't stop laughing.
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01:09 PM on 02/03/2011
Can't wait to see him back on screen again!
12:44 PM on 02/03/2011
Only one man will be ideal for Jennifer Aniston, and that man is me
 
 
Matthew, tell Jen to visit HP.
 
I'm not hard to find.
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12:52 PM on 02/03/2011
You can have her when I'm done with her.

I'll even put up with the smoking.
01:07 PM on 02/03/2011
Both of you are behind me in the line. Go ahead and fight it out.
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Lahonda
Bynocent Instander
03:02 PM on 02/03/2011
No, no, PRB is very hot... on fire actually. Could someone please pee on president Booth and put him out?
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Milash
It says I should edit my micro-bio, so I did.
12:29 PM on 02/03/2011
Love him. Call me!