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** With his co-star Reese Witherspoon on ''Film/CruelIntentions''. They were married for 9 years.

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** With his co-star Reese Witherspoon Creator/ReeseWitherspoon on ''Film/CruelIntentions''. They were married for 9 years.
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* MrFanservice: Arguably better known for his status as a MrFanservice than anything else, especially in his movies from the '90s where he'd often be shirtless in multiple scenes and completely naked in more than a few.
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** With his co-star Creator/Reese Witherspoon on ''Film/CruelIntentions''. They were married for 9 years.

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** With his co-star Creator/Reese Reese Witherspoon on ''Film/CruelIntentions''. They were married for 9 years.
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** With his co-star Reese Witherspoon on ''Film/CruelIntentions''.

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** With his co-star Reese Creator/Reese Witherspoon on ''Film/CruelIntentions''.''Film/CruelIntentions''. They were married for 9 years.
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* ''Film/Chaos2005''
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\n* ''Series/BigSky''

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** He auditioned for the role of [[Characters/StarWarsAnakinSkywalker Anakin Skywalker]] in ''Film/AttackOfTheClones'' before the casting of Creator/HaydenChristensen. However, he was turned down due to being considered "too young" at the time.
** He screen-tested for [[Characters/MCUCaptainAmerica Steve]] [[Comicbook/CaptainAmerica Rogers]] in the Franchise/MarvelCinematicUniverse before Creator/ChrisEvans was cast.
*** He was also approached for the part of [[Characters/MCUIronFist Danny]] [[Comicbook/IronFist Rand]] in ''{{Series/Iron Fist|2017}}'' before the casting of Creator/FinnJones.

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** He auditioned for the role of [[Characters/StarWarsAnakinSkywalker of Anakin Skywalker]] Skywalker in ''Film/AttackOfTheClones'' before the casting of Creator/HaydenChristensen. However, he was turned down due to being considered "too young" at the time.
** He screen-tested for [[Characters/MCUCaptainAmerica Steve]] for [[Comicbook/CaptainAmerica Steve Rogers]] in the Franchise/MarvelCinematicUniverse before Creator/ChrisEvans was cast.
*** He was also approached for the part of [[Characters/MCUIronFist Danny]] [[Comicbook/IronFist Danny Rand]] in ''{{Series/Iron Fist|2017}}'' before the casting of Creator/FinnJones.

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[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/ryan_phillippe.jpg]]

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[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/ryan_phillippe.jpg]]
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** He was offered the role of Anakin Skywalker in the ''Franchise/StarWars'' prequels, but turned it down, due to the age difference between himself and on-screen love interest Natalie Portman. There is seven years between them, and Natalie was barely eighteen when the second movie was to be filmed.
** He lost out on a role in ''Film/ThePatriot'' to Heath Ledger.

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** He was offered auditioned for the role of [[Characters/StarWarsAnakinSkywalker Anakin Skywalker Skywalker]] in ''Film/AttackOfTheClones'' before the casting of Creator/HaydenChristensen. However, he was turned down due to being considered "too young" at the time.
** He screen-tested for [[Characters/MCUCaptainAmerica Steve]] [[Comicbook/CaptainAmerica Rogers]]
in the ''Franchise/StarWars'' prequels, but turned it down, due to Franchise/MarvelCinematicUniverse before Creator/ChrisEvans was cast.
*** He was also approached for
the age difference between himself and on-screen love interest Natalie Portman. There is seven years between them, and Natalie was barely eighteen when part of [[Characters/MCUIronFist Danny]] [[Comicbook/IronFist Rand]] in ''{{Series/Iron Fist|2017}}'' before the second movie was to be filmed.
** He lost out on a role in ''Film/ThePatriot'' to Heath Ledger.
casting of Creator/FinnJones.
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** He was offered the role of Anakin Skywalker in the ''Film/StarWars'' prequels, but turned it down, due to the age difference between himself and on-screen love interest Natalie Portman. There is seven years between them, and Natalie was barely eighteen when the second movie was to be filmed.

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** He was offered the role of Anakin Skywalker in the ''Film/StarWars'' ''Franchise/StarWars'' prequels, but turned it down, due to the age difference between himself and on-screen love interest Natalie Portman. There is seven years between them, and Natalie was barely eighteen when the second movie was to be filmed.
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* ''54'' (film about the CoolestClubEver, ''Studio 54'')

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* ''54'' ''Film/FiftyFour'' (film about the CoolestClubEver, ''Studio 54'')
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* OlderThanHeLooks: Even in his late-30s to early-40s, he could probably still easily play any character in their mid or late 20s.
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\n* ''Series/{{Shooter}}''

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* HeReallyCanAct:

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* HeReallyCanAct:SugarWiki/HeReallyCanAct:
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* ''54'' (Film about the famous [[Main/{{Studio54}} Studio 54]] nightclub)

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* ''54'' (Film (film about the famous [[Main/{{Studio54}} Studio 54]] nightclub)CoolestClubEver, ''Studio 54'')



* PlayingAgainstType: Usually tough guys or DeadpanSnarkers in thrillers or action films, he stars in ''Film/MacGruber'' - a parody of such films.

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* PlayingAgainstType: Usually a tough guys guy or DeadpanSnarkers DeadpanSnarker in thrillers or action films, he stars in ''Film/MacGruber'' - a parody of such films.
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----
!!His career provides examples of:
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** He lost out on a role in ''Film/ThePatriot'' to Heath Ledger.

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** He lost out on a role in ''Film/ThePatriot'' to Heath Ledger.Ledger.
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Matthew Ryan Phillippe (September 10, 1974 - Present) was born in New Castle, Delaware, USA and is an actor, director and writer. After his stint as Billy Douglas on ABC's ''Series/OneLifeToLive'', he quickly rose to fame in the late 90s as a quintessential teen [[PrettyBoy heartthrob]] after his casting in ''Film/IKnowWhatYouDidLastSummer'' and ''Film/CruelIntentions''.

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Matthew Ryan Phillippe (September (born September 10, 1974 - Present) 1974) was born in New Castle, Delaware, USA and is an actor, director and writer. After his stint as Billy Douglas on ABC's ''Series/OneLifeToLive'', he quickly rose to fame in the late 90s as a quintessential teen [[PrettyBoy heartthrob]] after his casting in ''Film/IKnowWhatYouDidLastSummer'' and ''Film/CruelIntentions''.
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* ''Series/SecretsAndLies''

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* ''Series/SecretsAndLies''''Series/SecretsAndLies''

* DyeingForYourArt: Gained 25 lbs of muscle and stopped shaving for three months for ''The Way of the Gun''.
* FakeScot: Plays an apparently Scottish valet in ''Film/GosfordPark'' with a [[WhatTheHellIsThatAccent questionable accent]]. [[spoiler: He's really an undercover actor from Los Angeles]].
* HeReallyCanAct:
** His performance in ''Film/FlagsOfOurFathers'' was met with critical acclaim, and called the best of his career.
** Similarly he was heaped with praise for his portrayal of a ShellShockedVeteran in ''Film/StopLoss''. The film's director protested his casting but was quickly won over.
* PlayingAgainstType: Usually tough guys or DeadpanSnarkers in thrillers or action films, he stars in ''Film/MacGruber'' - a parody of such films.
* PlayingWithCharacterType: Playing his usual type of character...in the 1930s in ''Film/GosfordPark''.
* RomanceOnTheSet:
** With his co-star Reese Witherspoon on ''Film/CruelIntentions''.
** Also with Creator/AbbieCornish who he starred with in ''Film/StopLoss''.
* StarMakingRole: The one-two punches of ''Film/IKnowWhatYouDidLastSummer'' and ''Film/CruelIntentions'' put him on the map as a teen movie star in the late 90s.
* WhatCouldHaveBeen:
** He was offered the role of Anakin Skywalker in the ''Film/StarWars'' prequels, but turned it down, due to the age difference between himself and on-screen love interest Natalie Portman. There is seven years between them, and Natalie was barely eighteen when the second movie was to be filmed.
** He lost out on a role in ''Film/ThePatriot'' to Heath Ledger.
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* ''Film/GosfordPark''
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[[quoteright:350:http://static.tvtropes.org/pmwiki/pub/images/ryan_phillippe.jpg]]

Matthew Ryan Phillippe (September 10, 1974 - Present) was born in New Castle, Delaware, USA and is an actor, director and writer. After his stint as Billy Douglas on ABC's ''Series/OneLifeToLive'', he quickly rose to fame in the late 90s as a quintessential teen [[PrettyBoy heartthrob]] after his casting in ''Film/IKnowWhatYouDidLastSummer'' and ''Film/CruelIntentions''.

After a slight lull in his career, he began to rise again after his supporting role as the partner of a DirtyCop in the 2005-Best-Picture ''Film/{{Crash}}''. Soon to follow was his role in the critically-acclaimed war film ''Film/FlagsOfOurFathers'' directed by Creator/ClintEastwood, which is regarded as one of his best performances.

!!Ryan Phillippe's notable works:
[[AC:The '90s]]
* ''Series/OneLifeToLive''
* ''Film/CrimsonTide''
* ''Film/IKnowWhatYouDidLastSummer''
* ''54'' (Film about the famous [[Main/{{Studio54}} Studio 54]] nightclub)
* ''Film/CruelIntentions''

[[AC: The '00s]]
* ''Film/TheWayOfTheGun''
* ''Film/{{Antitrust}}''
* ''Film/{{Crash}}''
* ''Film/FlagsOfOurFathers''
* ''Film/{{Breach}}''
* ''Film/StopLoss''

[[AC: The '10s]]
* ''Series/{{Damages}}''
* ''Series/SecretsAndLies''

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