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1975, US, book (ISBN0-385-06099-8), _The Shootist_.
Author: Glendon Swarthout.
Dialog:
“Well?”
The doctor cleared his throat. “Books, every few days
I have to tell a man or a woman something I don’t want to.
I’m not very good at it. I have practiced medicine for
twenty-nine years, and I still don’t know how to do it well.”
“Call a spade a spade.”
“How old are you?”
“Fifty-one.”
“All right.” Hostetler crossed his legs. “You have
carcinoma of the prostate.”
“Carcinoma?”
“Cancer…”

1985, US, film: _Fletch_.
Character “Fletch” (Chevy Chase) sings “Moon River”
during prostate exam.

1988, US, film: _Who Framed Roger Rabbit_.
Dialog:
Roger Rabbit: Yeah. Check the probate. Why, my Uncle
Thumper had a problem with HIS probate, and he
had to take these big pills, and drink lots of water.
Eddie Valiant: Not prostate, you idiot, PROBATE!

1995, US, film: _Father of the Bride Part II_.
Character “Prostate Nurse” played by Wendy Worthington.
Character “Prostate Doctor” played by Harris Laskawy.

1995, US, TV: _Lois & Clark: The New Adventures of Superman_.
Episode #2.12: “The Eyes Have It”
Dialog:
Jimmy Olsen: Lois, have you seen Clark? I need to talk to him.
Lois Lane: You can talk to me.
Jimmy Olsen: It’s a guy thing.
Lois Lane: That means it’s about prostate trouble or about
women. You’re too young for prostate trouble. That means
you wanna talk to Clark about women.

1997, US, film: _Fathers’ Day_
Dialog:
Dale Putley: I wrote this musical called “Hello, Doctor,
it’s Still Swollen.” It had a great opening, went
like this: “Hello Mr. Colon, my prostate’s feelin’
swollen. I think that things are flowin’ not so well.”
[Knock on the door]
Dale Putley: Breakfast! “I’m feelin’ kinda heinous cause
there’s something in my…”
Waiter: Morning!

2001, US, film: _Zoolander_.
Quote from character “Maury Ballstein”:
“I’ve got a prostate the size of a honeydew and a head
full of bad memories.”

2001-02-18, US, TV: _Lifestyle Magazine_ Season 18.
Episode 07: “The Prostate Problem: How to Help Your Man”

2002-02-##, UK, live comedy act: “Jack Dee: Live at
the [Hammersmith] Apollo”
http://www.imdb.com/title/tt1175501/
Dee covers his thoughts on the internet, prostate problems,
old people, children and other topics that get his goat.

2003-02-15, Canada, TV, John Zaritsky: “Men Don’t Cry:
Prostate Cancer Stories”.
http://www.imdb.com/title/tt0420773/

2003-11-12, UK, TV comedy series: _”Becker_ Season 6.
http://www.imdb.com/title/tt0520554/
Episode 6: “Afterglow”, directed by Chris Brougham.
Character “Mr. Prostate” played by Wayne Thomas Yorke.

2004, US, TV: _CSI: Crime Scene Investigation_
http://www.imdb.com/character/ch0011027/quotes
Episode 5.2: “Down the Drain”
Dialog:
Greg Sanders: What are you doing?
Gil Grissom: Good, you’re here.
[tosses him a plastic cup]
Gil Grissom: Fill this up for me, will ya.
Greg Sanders: With what?
Gil Grissom: It’s a urine specimen cup, Greg, what do you think?
Greg Sanders: [looks at the cup again]
[pauses]
Greg Sanders: Okay.
Gil Grissom: That took a long time. You may need a prostate exam.
Greg Sanders: My prostate is just fine!

2005-02-09, US, TV: _Healthy Body, Healthy Mind_, Season 3.
Episode 2: “Advanced Prostate Cancer”, Director: Bob Buruchian.
http://www.imdb.com/title/tt1273953/

2005-02-20, US, TV: _Robot Chicken_ “Junk in the Trunk”
http://www.imdb.com/title/tt0687776/
Bloopers:
[…] The heroin part is probably the funniest, but so is the
transformers, they are in a locker room being dumb. Then a
transformer gets prostate cancer. Bloopers is pretty good too.
I don’t know why, but i thought the Pokémon part was really fun.
Otherwise, the most more i can say is that you should find a
way to watch this and other episodes.

2006-09-10, US, TV: _Family Guy_, Season 5.
Episode 1: “Stewie Loves Lois”.
Synopsis:
Peter agrees to undergo a prostate exam, not knowing how it
works. He feels raped when his doctor tries to examine him.
When he finds out all his friends have had the same experience,
he decides to sue his doctor for rape.
Dialog:
Peter Griffin: What the hell was that?
Dr. Hartman: Mr. Griffin, that was a prostate exam.
Peter Griffin: Shut up! You had your finger in my ass!

2004-09, US, TV: _Rescue Me_.
Synopsis:
Amongst the deceased/transferred firefighters is Billy Warren
(played by Ed Sullivan). It was revealed in the pilot episode
that Billy may have been diagnosed with prostate cancer, which
may explain his behavior and outlook on life. He was very popular
with women and, as was revealed by his widow after his funeral,
had a 10-inch penis, winning him an in-house contest over who
had the largest penis. He appears as one of Tommy’s “ghosts”
during season two, three, and four, condemning Tommy over his
various actions, and shows up again in season five with all
of the other ghosts when Tommy starts drinking again.

2007, UK, TV campaign for prostate cancer charity.
Synopsis:
TV comedian Robert Monkhouse died of prostate cancer in 2003.
Yet in 2007 he made a “comeback”, appearing in a new TV
campaign advertising a prostate cancer charity. The ad,
made with the blessing of his widow, blends footage of
Monkhouse with that of a body double then adds CGI
manipulation of his face to match what is being spoken
by a sound-double.

2008, US, TV talkshow _Bedside Manor_ Season 2.
Episode 18: “Prostate Problems”.
Character “Prostate Patient” played by Dave Vescio.