That’s 7 actors.
I was going by movies, oops.
I will try a different route,
Vinnie Jones was in Lock, Stock with Jason Statham,
Jason Statham was in the Expendables with Sylvester Stallone,
Stallone was in Tango & Cash with Kurt Russell,
Kurt Russell was with Dave Bautista in Guardians of the Galaxy vol. 2,
Dave Bautista, who was in WWE Raw, like Dwayne “The Rock” Johnson.
Hopefully better this time…
(I’m very bad at this game so I’m writing software to play it for me. Not as competition, just to see what it comes up with – and to learn a bit more Rust.)
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Okay, had to look up Greg Kinnear films. Then I had to think of the silliest way possible to start this. It was going to be Matt Damon in Thor: Ragnarok, but then I thought of something better!
Matt Damon was in Deadpool 2 with Alan Tudyk
Tudyk was in 28 Days with Sandra Bullock
Bullock was in Demolition Man with Sylvester Stallone
Stallone was in First Blood with Richard Crenna
Crenna was in Sabrina with Greg Kinnear
Next up: Jennifer Lawrence to Jennifer Lopez
I just went with something random 
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Jennifer Lawrence was in Silver Linings with Bradley Cooper,
Cooper was in Wedding Crashers with Will Ferrell
Will Ferrell was great as Mugatu in Zoolander, with Owen Wilson playing Hansel.
Wilson was in the Internship with Vince Vaughn,
Vaughn was a crooked farmer in Into the Wild, a film directed by Sean Penn
Sean Penn was in U Turn with Jennifer Lopez
Gosh, I struggled to do it more than 4… I had U Turn clear from the beginning, as Into the Wild with Vince Vaughn… the problem was extending it before arriving to Wedding Crashers too early.
Anybody fancy linking Wesley Snipes to Viola Davis?
You have seven again 
Wait a minute, I forgot to remove Will Ferrell 
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Ah, I would’ve gone with him in Eurotrip.
I had a flash of inspiration in the shower 
Wesley Snipes was in Blade: Trinity with Parker Posey
who was in Josie and the Pussycats with Alan Cumming
who was in Spice World with Meat Loaf
who was in Fight Club with Jared Leto
who was in Suicide Squad with Viola Davis
(A lot of bad films in that one.)
Next up: Human Torch to Human Torch - Chris Evans to Michael B Jordan without using anything based on a Marvel property.
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I can do it in 2…
A random one I did, because I misremembered my own challenge 
Dave Bautista was in Guardians of the Galaxy with Nathan Fillion
who was in Firefly with Morena Baccarin
who was in Deadpool 2 with Julian Dennison
who was in Hunt for the Wilderpeople with Rachel House
who was in Moana with Dwayne “The Rock” Johnson
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Yes, but the challenge is in stretching it to 6.
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I know - I was trying to do it in 6 but just kept coming back to doing it in 2, several different ways!
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I’d say the challenge is not to do it in 7…!
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Chris Evans was in Push with Dakota Fanning (please don’t be Marvel),
Fanning was in Hide and Seek with Robert DeNiro,
DeNiro was in Casino with Sharon Stone,
Sharon Stone starred along Sylvester Stallone in The Specialist,
And Sly was in Creed with Michael B Jordan.
If I did not screw up (again) maybe Chris Pratt to Chris Pine without Star Trek or Marvel movies?
Two again. Damnit
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No DC movies either (as Pine is in Wonder Woman)! But two films owned by Disney and one based on a comic
Chris Pratt was in Wanted with Angelina Jolie
who was in Lara Croft: Tomb Raider with Daniel Craig
who was in Star Wars: The Force Awakens with Daisy Ridley
who was in Murder on the Orient Express with Johnny Depp
who was in Into the Woods with Chris Pine
Musicians turned actors: David Bowie to Lady Gaga
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Oh, I would have gone from Marvel to DC on purpose. I forgot he was in Wonder Woman (maybe because I have not seen any of them)
Completely forgot about him on that movie!