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The Donald (Donald Trump): New this season on The Apprentice: I’ve digitally remastered videos of myself from the 80s and 90s to compete against each other. Can’t wait to fire myself.
Twitter Historian on September 21st 2009 in 21st Century, Entertainment

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Bill Lumbergh: @petergibbons What’s happening? Yeah… we’re putting new cover sheets on all the #TPSreports. Did my DM get lost in your tweetstream?
Submitted by Brett Abel — Thanks Brett!
[from the 1999 film Office Space]
Twitter Historian on September 18th 2009 in 1990s, Entertainment

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From Twitterstorian “LC” comes this 80s flashback…

LilArnoldJ: What you tweetin’ ’bout, @Willis?
Twitter Historian on September 17th 2009 in 1980s, Entertainment, Submitted

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Kane: @Rosebud!
Idea submitted by Luis Villalobos
Twitter Historian on September 7th 2009 in 1900-1950, Entertainment

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Gatsby: @TomBuchanan Only a bathtub full of mint juleps could make this situation more awkward.
Suggested by Carol Caywood
Twitter Historian on September 7th 2009 in 1900-1950, Entertainment