Neil Diamond was in Saving Silverman with Jack Black,
Black had a cameo in Anchorman: The Legend of Ron Bergundy with Will Ferrell,
Ferrell was in Austin Powers: International Man of Mystery with Mike Myers,
Myers was in Wayne's World with Alice Cooper.

How about Sidney Poitier to Denzel Washington.

Sidney Poitier was in Sneakers with Stephen Tobolowsky
Stephen Tobolowsky was in View from the Top with Rob Lowe
Rob Lowe was in Austin Powers: The Spy Who Shagged Me with Charles Napier
Charles Napier was in The Manchurian Candidate with Denzel Washington


Marc Anthony to Martin Boddey
IMDB lists 3 Marc A. so any one of them your choice

Marc Anthony was in Man on Fire with Christopher Walken
Walken was in Batman Returns with Michelle Pfeifer
Michelle was in What Lies Beneath with Harrison Ford
Ford was in Star Wars: A New Hope with Peter Cushing
and Cushing was in The Naked Edge with Martin Boddey


Bob Geldof to Bobcat Goldthwait

Bobcat Goldthwaite was in Blow with Johnny Depp
Johnny Depp is in Corpse Bride (Tim Burton's new flick (after Charlie and the Chocolate Factory, of course)--looks good, too) with Helena Bonham Carter
Helena Bonham Carter was in Fight Club with Meat Loaf
Meat Loaf was in Spice World (bahahahahaha....Spice World) with Bob Geldof


David Bowie to Isaac Freeman

David Bowie was in Twin Peaks: Fire Walk with Me with David Lynch
David Lynch was in Epreuves d'artistes with Clint Eastwood
Clint Eastwood was in A Perfect World with Ray McKinnon
Ray McKinnon was in O Brother, Where Art Thou? with Issac Freeman


Morgan Freeman to James Earl Jones

Cake

Morgan Freeman was in Batman Begins with Gary Oldman
Oldman was in Air Force One with Harrison Ford
Ford was in Star Wars: A new hope with James Earl Jones

Eminem to Frank Sinatra

Sinatra was in Cannonball Run II with Jackie Chan
who was in The Tuxedo with Jason Issacs
who was in Black Hawk Down with Josh Hartnett
who was in Sin City with Brittney Murphy
who was in 8 Mile with Eminem

try

Sammy Davis Jr. to Ludacris

Sammy Davis Jr was in Cannonball Run II with Tony Danza
TD was in Crash with Ludacris

How about Crispin Glover to Danny Glover

Easily done.

Crispin Glover was in Charlie's Angels: Full Throttle with John Cleese
and Cleese was in Silverado with Danny Glover


Gordon Jump to Frank Bonner (bonus points for knowing why I paired 'em)

Arthur 'Big Guy' Carlson aka:Frank Bonner was in A Light in the Forest with Bernie Kopell
Bernie Kopell was in Dismembered with Herbert 'Herb' Tarlek aka:Gordon Jump

WKRP in Cincinnati

Howard Hesseman to Gary Sandy

Quite well done, Sam, except for a small detail... you reversed your actors (Gordon Jump was the Big Guy)

Howard Hesseman was in About Schmidt with Dermot Mulroney
Dermot (what an odd name) was in Young Guns with Lou Diamond Phillips
Chavez was in Courage Under Fire with Michael Moriarty
and Moriarty was in Troll with Gary Sandy


I'm enjoying this one... Jan Smithers to Tim Reid

Bailey Quarters aka:Jan Smithers was in When the North Wind Blows with Henry Brandon
Henry Brandon was in The Big Fisherman with Herbert Lom
Herbert Lom was in Master of Dragonard Hill with Eartha Kitt
Eartha Kitt was in On the One with Venus Flytrap aka:Gordon Sims,Tim Reid


dyslexia on curses my.........curse on my dyslexia

Carol Bruce to Sylvia Sidney or
Mama Carlson to Mama Carlson

Carol Bruce was in Planes Trains and Automobiles with Steve Martin
Steve Martin was in Three Amigos with Martin Short
Martin Short was in Mars Attacks! with Sylvia Sidney

Elliott Gould to Wayne Rogers

How about Elliot Gould was in Oceans 11 (or 12) with Scott Caan
SC was in In Enemy Hands with William H Macy
WHM was in Ghosts of Mississippi with Wayne Rogers

I like the current theme...

How about Dick York to Will Farrell
*** never mind *** (Already done, doh)

New one...
James Caan to Kirk Douglas

That one was on the previous page.

Edited my original post to change the new link. I forgot that one was done already. Thanks RioD.

James Caan was in Misery with Lauren Bacall
Lauren Bacall was in Diamonds Kirk Douglas


Sidney Poitier to Ashton Kutcher

Bonus points if you know why...

They've both gotten into Demi's pants?

Sidney Poitier was in Sneakers with Dan Ayckroyd
Elwood was in Evolution with Ethan Suplee
and Ethan Suplee was in Butterfly Effect with Ashton Kutcher


Christopher Lambert to Natasha Henstridge

Christopher Lambert was in Highlander Endgame with Adrian Paul
who was in The Breed with Bokeem Woodbine
He was in Dead Presidents with Chris Tucker
who was in Friday with Ice Cube
who was in Ghost Of Mars with Natasha Henstridge

How about

Eve to Christian Bale

Eve was in Cookout with Reg Cathey
Reg Cathey was in American Psycho with Christian Bale

Back to the TV:

Phil Silvers to Steve Martin

[EDIT] Regarding Sidney Poitier and Ashton Kutcher; They both "came to dinner".

Of course, points to RioD...and vomit on my shoes at the remake...Points also to UTM for classic answer.

Phil Silvers was in It's a Mad Mad Mad Mad World with Milton Berle
Milton Berle was in The Muppet Movie with Steve Martin

Live from New York, it's

Gilda Radner to Phil Hartman

Gilda Radner was in Hanky Panky with Gene Wilder
Gene Wilder was in Blazing Saddles with Harvey Korman
Harvey Korman was in Jingle All The Way with Phil Hartman

I still like the 'same characer' theme...

Peter Cook to Elizabeth Hurley

Peter Cook was the Impressive Clergyman (Mawwiage... mawwiage is what bwings us togevwer... todayy...) in The Princess Bride with Cary Elwes
Elwes was in Twister with Bill Paxton
Paxton was in True Lies with Tom Arnold
and Tom Arnold was in Austin Powers: International Man of Mystery with Liz Hurley


Grace Jones to Grace Kelly

Grace Jones was in A View To A Kill with Roger Moore
Roger Moore was in The Sins of Rachel Cade with Angie Dickenson
Angie Dickenson was in Poppies Are Also Flowers with Grace Kelly

Try Robert Culp to Owen Wilson

(figured Bill Cosby to Eddie Murphy would be too easy)

Robert Culp was in Turk 182! (one of my all-time favorite flicks) with Robert Urich
Urich was in Ice Pirates with Anjelica Huston
Huston was in Ever After with Drew Barrymore
Drew Barrymore was in Charlie's Angels with Lucy Liu
and Liu was in Shanghai Noon with Owen Wilson

(I even managed to connect 'em with movies I own )

Bruce Vilanch to Bruce Boxleitner

Bruce Vilanch was in The Aristocrats with Kevin Pollak
Kevin Pollak was in The Whole Ten Yards with Natasha Henstridge
Natasha Henstridge was in Riders with Frank Fontaine
Frank Fontaine was in Life in the Balance with Bruce Boxleitner

points if you know why
Frank Sinatra to George Clooney

Sinatra was in Cannonball Run II with Burt Reynolds
he was in The Longest Yard with Adam Sandler
who was in Mr. Deeds with Winonna Rider
the shoplifter was in Autumn In New York with Richard Gere
he was in Runaway Bride with Julia Roberts
she was in Ocean's Eleven with George Clooney

Humphrey Bogart to Alyson Hannigan

Sorry didn't mean to double post

Humphrey Bogart was in The Harder They Fall with Rod Steiger
Rod Steiger was in The Hollywood Sign with Burt Reynolds
Burt Reynolds was in Hustle with Fred Willard
Fred Willard was in American Wedding with Alyson Hannigan


Bokeem Woodbine to Alisa Reyes

Bokeem was in Ray with Jamie Fox
Fox was in Ali with Will Smith
Smith was in Independence Day with Bill Pullman
Pullman was in Lost Highway with Gary Busey
and Busey was in A Sight for Sore Eyes with Alisa Reyes


Christine Baranski to Crystal Bernard

Christine Baranski was in Bowfinger with Steve Martin
Steve Martin was in Roxanne with Daryl Hannah
Daryl Hannah was in Jackpot with Crystal Bernard


Tia Matza to Tia Carrere

Tia Matza was in Jackpot with Daryl Hannah
Hannah was in Splash with Tom Hanks
Hanks was in Apollo 13 with Bill Paxton
and Paxton was in True Lies with Tia Carrere


Jenna Elfman to Danny Elfman

Danny Elfman was in Big Fish with Steve Buscemi
SB was in Airheads with Brendon Fraser
BF was in Loony Toons:Back in Action with Jenna "Dharma" Elfman

How about Steven Tyler to Liv Tyler

here goes...

Steven Tyler was in Wayne's World 2 with Tia Carrera(sp?)
Nani was in True Lies with Bill Paxton
Chet was in Apollo 13 with Tom Hanks
Forrest was in That Thing You Do! with Liv Tyler


OK... Willard Scott to Renee Zellweger

Willard Scott was in Holy Man with Kelly Preston
KP was in Jerry Maguire with Rene Zellweger


How about a sports theme...
Cam Neeley to Shaquille O'Neal

damn that Kelly Preston!

OK...

Cam Neely was in D2: The Mighty Ducks with Emilio Estevez
Charlie Sheen's brother was in St. Elmo's Fire with Judd Nelson
Bender was in Steel with Shaquille O'Neal

whee!

let's do:

charlize theron to ian mckellen

Charlize Theron was in Devil's Advocate with Keanu Reeves
Keanu was in The Matrix with Hugo Weaving
and Weaving was in Lord of the Rings: Return of the King with Sir Ian McKellen


Queen Latifah to Jamie King.

Queen Latifah was in Hoodlum with Andy Garcia
Andy Garcia was in Ocean's Twelve with Matt Damon
Matt Damon was in Stuck On You with Jessica Cauffiel
Jessica Cauffiel was in White Chicks with Jaime King


Jennifer Garner to James Garner

Jennifer Garner was in Daredevil with Michael Clarke Duncan
Duncan was in The Green Mile with Tom Hanks
Hanks was in Forrest Gump with Sally Field
and Sally was in Murphy's Romance with the great James Garner


Oprah to Uma.

UTM since you didn't specify last names I had some fun with this one

Oprah Winfrey was in Native Son with Sarah Silver
Sarah Silver was in Hollywood Homicide with Harrison Ford
Harrison Ford was in Indiana Jones and the Temple of Doom with Amrish Puri
Amrish Puri was in Censor with Uma (she's from India)


Johnny Depp(aka: Oprah Noodlemantra) was in Freddy's Dead: The Final Nightmare with Robert Englund
Robert Englund was in New Nightmare with John Saxon
John Saxon was in Shalimar with Aruna Irani
Aruna Irani was in Censor with Uma

Assuming you meant Uma Thurman

Oprah Winfrey was in Beloved with Danny Glover
Danny Glover was in Chu Chu and the Philly Flash with Sid Haig
Sid Haig was in Kill Bill: Vol. 2 with Uma Thurman

Johnny Depp(aka: Oprah Noodlemantra) was in Donnie Brasco with Michael Madsen
Michael Madsen was in Kill Bill: Vol. 2 with Uma Thurman

Brian Willis to Bruce Willis

you're insane Sam...

OK... had to look up Brian Willis *shrug*

Brian Willis was in Hook with Maggie Smith
Professor McGonnegal was in all 3 Harry Potter films with Alan Rickman
Professor Snape was in Die Hard with Bruce Willis

woo!

how 'bout:

jeanne tripplehorn -to- trip hamilton

Hmmm... And I had to look up Trip Hamilton...

Trip hamilton was in The Legend of Bagger Vance with Will Smith
Willie was in I Robot with Bruce Greenwood
Bruce was in Thirteen Days with Kevin Costner
Mr. Costner was in that epic Waterworld with Jeanne Tripplehorn


How about Rip Torn to Rip Taylor...

Rip Taylor was in Jackass: The Movie with Johnny Knoxville
and Knoxville was in Men in Black II with Rip Torn


Shelley Long to Kirstie Alley

Rip Torn was in Men in Black II with Gene Lebell
Gene LeBell was in Jackass: The Movie with Rip Taylor

I'm getting to slow UTM beat me but a full 3 minutes


Shelley Long was in A Very Brady Sequel with Brian Van Holt
Brian Van Holt was in Basic with John Travolta
John Travolta was in Look Who's Talking Now with Kirstie Alley

Danny Glover to Crispin Glover
holy crap old age sucks

ok so

Bruce Willis to Matthew McConaughey

You must be slipping, Sam. We just did the Crispin Glover - Danny Glover thing a page back.

Crispin Glover was in Charlie's Angels: Full Throttle with John Cleese
and Cleese was in Silverado with Danny Glover

It's early Morning and I havent had my cuppa.....

but I fixed it but good!!

That one's easy... McConaughey was in A Time to Kill with Sam Jackson
and Jackson has been in multiple movies (including Unbreakable) with Bruce Willis.


Brad Garrett to Howie Mandell

Brad Garrett was in Garfield with Alan Cumming
AC was in The Anniversary Party with Phoebe Cates
PC was in Gremlins with Howie Mandel (his voice anyway - Gizmo!)

How about Judge Reinhold to Judd Hirsch.

Judge Reinhold was in Beverly Hills Cop with Eddie Murphy
Murphy was in Bowfinger with Heather Graham
Heather was in Boogie Nights with Julianne Moore
Julianne Moore was in The Lost World with Jeff Goldblum
and Goldblum was in Independence Day with Judd Hirsch.

Now... Rock Hudson to The Rock