Cameron Diaz was in Charlies Angels: Full Throttle with Drew Barrymore who starred in and produced Donnie Darko with Daveigh Chase who played the lead role in its sequel S. darko with Ed Westwick (Gossip Girl) AND James Lafferty (One Tree Hill)
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Laura Sim(16:40:13) :
Cameron Diaz starred in the Charlies Angels which McG directed who also produced episodes of The OC
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teendramawhore(17:19:30) :
Laura: Dang, you made it so easy. Good job!
Izzie: Double connection! Well done!
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Em(19:10:36) :
Cameron Diaz starred in Vanilla Sky with Tom Cruise, who starred in War of the Worlds with Dakota Fanning, who starred in The Secret Life of Bees with Tristan Wilds (90210) and Hilarie Burton (One Tree Hill).
or
Cameron Diaz starred in My sister’s keeper with Abigail Breslin who guest starred on What I Like About You which starred Jennie Garth (BH 90210)
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Alyssa(20:05:05) :
Cameron Diaz was in Gangs of New York with Leo DiCaprio and so all of his connections then apply 😉
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teendramawhore(20:19:59) :
Em: Nice double connection you got as well! I had no idea Abigail was on What I Like About You (then again, I’ve only seen like 2 episodes).
Alyssa: Jeez Louise. I need to step up my game!
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teendramawhore(00:18:56) :
Oh, I just thought of what should’ve been an obvious one! Cameron Diaz starred in Vanilla Sky with Tom Cruise (and I think they’re working on a new movie together, too)–and Tom is married to Katie Holmes (Joey, Dawson’s Creek)!
We can go obvious with Cameron Diaz worked with Drew Barrymore who was in Scream which starred Courtney Cox who works with Busy Philipps who was on Dawson’s Creek
I got an obscure one for you which ends the same. Cameron Diaz was in The Sweetest Thing with Selma Blair who was in Can’t Hardly Wait with Jason Segel who was in Freeks and Geeks which also starred Busy Philipps who was in Dawson’s Creek.
Or
Cameron Diaz worked with Johnny Messner on ‘The Sweetest Thing’ who guest starred on The OC
We could also go Cameron Diaz has been on Saturday Night Live and so has Katie Holmes and other teen drama actors.
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teendramawhore(01:39:28) :
Mega, those are all great! Thank you!
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Step(22:28:11) :
If we can include who dated who: Cameron Diaz dated Justin Timberlake who dated Alyssa Milano who was on “Charmed” with Shannen Doherty from “90210”.
if not:
Cameron Diaz was in “The Holiday” with Jack Black who was in “School of Rock” with Miranda Cosgrove who was on “Drake and Josh” which Allison Stoner guest-starred on, who was in “Cheaper by the Dozen” with Tom Welling, who stas on “Supernatural” which guest-starred Tori Spelling of “90210”.
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teendramawhore(23:05:57) :
Traditionally the game only uses media (movies, TV, etc.) to connect people but I think for our purposes, relationships are fine.
But I think you mean Tom welling stars on Smallville? Either way, you’re right. And Brian Austin Green (David, BH90210) guest-starred on it as well!
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Step(15:48:21) :
Ok sounds good! Oh yeah, I meant Smallville, haha! I was doing it from memory so it got mixed up in my mind. I think Tori Spelling guest-starred on “Smallville”, too, come to think of it!
TeenDramaWhore 
Cameron Diaz was in Charlies Angels: Full Throttle with Drew Barrymore who starred in and produced Donnie Darko with Daveigh Chase who played the lead role in its sequel S. darko with Ed Westwick (Gossip Girl) AND James Lafferty (One Tree Hill)
Cameron Diaz starred in the Charlies Angels which McG directed who also produced episodes of The OC
Laura: Dang, you made it so easy. Good job!
Izzie: Double connection! Well done!
Cameron Diaz starred in Vanilla Sky with Tom Cruise, who starred in War of the Worlds with Dakota Fanning, who starred in The Secret Life of Bees with Tristan Wilds (90210) and Hilarie Burton (One Tree Hill).
or
Cameron Diaz starred in My sister’s keeper with Abigail Breslin who guest starred on What I Like About You which starred Jennie Garth (BH 90210)
Cameron Diaz was in Gangs of New York with Leo DiCaprio and so all of his connections then apply 😉
Em: Nice double connection you got as well! I had no idea Abigail was on What I Like About You (then again, I’ve only seen like 2 episodes).
Alyssa: Jeez Louise. I need to step up my game!
Oh, I just thought of what should’ve been an obvious one! Cameron Diaz starred in Vanilla Sky with Tom Cruise (and I think they’re working on a new movie together, too)–and Tom is married to Katie Holmes (Joey, Dawson’s Creek)!
We can go obvious with Cameron Diaz worked with Drew Barrymore who was in Scream which starred Courtney Cox who works with Busy Philipps who was on Dawson’s Creek
I got an obscure one for you which ends the same. Cameron Diaz was in The Sweetest Thing with Selma Blair who was in Can’t Hardly Wait with Jason Segel who was in Freeks and Geeks which also starred Busy Philipps who was in Dawson’s Creek.
Or
Cameron Diaz worked with Johnny Messner on ‘The Sweetest Thing’ who guest starred on The OC
We could also go Cameron Diaz has been on Saturday Night Live and so has Katie Holmes and other teen drama actors.
Mega, those are all great! Thank you!
If we can include who dated who: Cameron Diaz dated Justin Timberlake who dated Alyssa Milano who was on “Charmed” with Shannen Doherty from “90210”.
if not:
Cameron Diaz was in “The Holiday” with Jack Black who was in “School of Rock” with Miranda Cosgrove who was on “Drake and Josh” which Allison Stoner guest-starred on, who was in “Cheaper by the Dozen” with Tom Welling, who stas on “Supernatural” which guest-starred Tori Spelling of “90210”.
Traditionally the game only uses media (movies, TV, etc.) to connect people but I think for our purposes, relationships are fine.
But I think you mean Tom welling stars on Smallville? Either way, you’re right. And Brian Austin Green (David, BH90210) guest-starred on it as well!
Ok sounds good! Oh yeah, I meant Smallville, haha! I was doing it from memory so it got mixed up in my mind. I think Tori Spelling guest-starred on “Smallville”, too, come to think of it!