One of these things just doesn't belong

Group 1:

Roger Ward – Young Einstein (1988)
André René Roussimoff – The Princess Bride (1987)
James George Janos – Predator (1987)
Terry Bollea – Rocky III (1982)
Laurence Tureaud – D.C. Cab (1983)

All actors are former wrestlers. Of these, only Andre "the Giant" Roussimoff has been featured on a Dead Wrestler Trading Card
***

Group 2:

Cool World (1992)
Who Framed Roger Rabbit (1988)
The Incredible Mr. Limpet (1964)
Kill Bill, Vol 1 (2003)
Space Jam (1996)

All films feature a combination of live-action and animation. Only in Kill Bill, Volume 1 do these two media fail to interact.
***

Group 3:

Gone in Sixty Seconds (2000)
The Thomas Crown Affair (1999)
Dirty Rotten Scoundrels (1988)
I Am Legend (2007)
Never Say Never Again (1983)

All films are remakes of previous films:
Gone in 60 Seconds (1974)
The Thomas Crown Affair (1968)
Bedtime Story (1964)
The Omega Man (1971)
Thunderball (1965)

Only The Thomas Crown Affair retained the same title in both films
***

Group 4:

Mad Max (1979)
Yojimbo (1961)
Fistful of Dollars (Per un pugno di dollari) (1964)
Old Boy (2003)
Wild at Heart (1989)

All five films feature a severed human hand. Only Old Boy fails to have this severed hand interact with a dog.

The bonus bonus? I've never seen D.C. Cab, Space Jam, or I Am Legend.

Holli Wouldn't Cheat Like This...

The Kims:

Bassinger - Holli Would (Cool World)
Cattrall - Gracie Law (Big Trouble in Little China)
Darby - Mattie Ross (True Grit)
Delaney - Detective Diane Russell (NYPD Blue)
Fields - Dorothy 'Tootie' Ramsey (The Facts of Life)
Hunter - Zira (Planet of the Apes)
Jones - Tina Parker (Juwanna Mann)
Kardashian - Summa Eve (Deep In the Valley aka Hot Babes)
Novak - Madeleine Elster & Judy Barton (Vertigo)

Spoilers - Recursion

Hey, cheater!  Go here for the questions before you read all the answers!

 

Films featured in a later film:

Rambo - Son of Rambo
Casablanca - When Harry met Sally
Rio Bravo - Get Shorty
Touch of Evil - Sneakers/Get Shorty
Goldfinger - Catch Me if You Can
Spartacus - Clueless
Miracle on 34th Street - Home Alone
Captain Blood - The Goonies
Watership Down - Donnie Darko
Myrt and Marge - O Brother, Where Art Thou?
It's a Wonderful Life - Bruce Almighty/Scrooged
Gilda - The Fisher King/The Shawshank Redemption

Name two movies that feature video stores, though no actual film footage is ever seen:

Gross Pointe Blank
Clerks

Name two movies that feature fake films as part of the main film's plotline.

Purple Rose of Cairo
Singin' in the Rain
Last Action Hero
For Your Consideration
Jay and Silent Bob Strike Back

Name two movies that feature 'themselves' in the film.

Spaceballs
Singin' in the Rain
Blazing Saddles

Sure, there are more answers than I requested.  That's why you should have done better than you did.  Now look sad and say "d'oh."