Ofc this is my take on the characters, but I'm going to go through each of the more obvious characters for an expansion/a sequel:
Sam & Max
X Sam (he'd have a few stories but he's too predictable and monotonous for an entertaining poker game)
X Bosco (funny as hell in the games but wouldn't really fit in to the poker game as an entertaining character)
X Sybil (can't see how she could be any less boring than in the games)
X Ms Bosco (not complex enough a character)
Strong Bad/Homestar Runner
They'd be great all in the same poker game together but only the following strike me as worthy additions:
King of Town
Pompom
Team Fortress
I don't know the franchise at all so this is a pure guess
Spy
Penny Arcade
Gabe (could be hilarious, especially in interactions with Morgan Le Flay)
Monkey Island
X Guybrush (he'd think his strategy aloud and inadvertently tell everyone his hand)
X Elaine (not complex or funny enough character)
Voodoo Lady (a bit monotonous and predictable but could also be very funny)
LeChuck (strong and sneaky, aka someone Heavy would look up to, as well as being very funny)
X Stan (not suited to the setting, at all)
Herman Toothrot (maybe only because he's funny and we'd see some character development)
Morgan (would be the female, schoolgirl aggressive version of Tycho, someone for Gabe to wind up)
Wallace & Gromit
X Wallace (too boring and predictable)
X Gromit (brilliant faces but wouldn't be able to take part in conversations)
X Penguin/Chicken (see above)
X Cooker (see above)
X Preston (see above)
X All Wallace's former love interests (not fitting to the situation)
Bone
X Fone (too much of a one-dimensional character)
X Phoney (see above)
X Smiley (see above)
X Thorn (see above)
Rose
X Dragon (wouldn't fit in the shot very well)
Puzzle Agent
X Nelson (his personality would be too flat in a scenario like this)
Back to the Future
X Marty (similar in personality for this setting as Tycho Brahe, Fone Bone and Nelson Tethers)
X Doc Brown (a mad-but-good scientist stereotype would not fit this game if we're still playing poker)
Biff (could be rather like Strong Bad but in hard mode, would have the Armanak with him so would be like Max with Futurevision(tm))
Jurassic Park
Nobody would be suitable.
Not followed CSI or Telltale Texas Hold-em at all so cant comment on those.
Very funny but you could apply that to all the Homestar Runner and Penny Arcade characters, many whom I'd like to see/enjoyed seeing in Poker Night at the Inventory.
Wallace & Gromit
X Wallace (too boring and predictable)
X Gromit (brilliant faces but wouldn't be able to take part in conversations)
X Penguin/Chicken (see above)
X Cooker (see above)
X Preston (see above)
X All Wallace's former love interests (not fitting to the situation)
What about Monty Muzzle from episode 3 of Wallace & Gromit's Grand Adventures? He seems a good choice for a poker game, considering his con man style.
McPhail, does the word "copyright" mean anything to you?
It would be nice to have some of them, but I don't think Telltale would have the time or patience to secure the necessary rights to those characters, with the notable exception of Scout, who could actually get in the game considering that Telltale has previously cooperated with Valve for Poker Night and TF2.
If the characters had to be from the same series, I would have to pick Gabe, Sam, the Scout, and Homestar Runner. However, if the characters could be from any series, I would pick Notch (he counts, right?), Duke Nukem, the Scout, and Ellis.
Comments
Obviously Gabe and Sam. That'd be cool.
Snipah, to be the straight man.
And Strong Sad. I...I just really want to spend an hour with him and chill.
Sal (from the afterlife)
Agent Nelson Tethers "This pattern of cards looks like a puzzle !!"
Beelzebub
Sam & Max
X Sam (he'd have a few stories but he's too predictable and monotonous for an entertaining poker game)
X Bosco (funny as hell in the games but wouldn't really fit in to the poker game as an entertaining character)
X Sybil (can't see how she could be any less boring than in the games)
X Ms Bosco (not complex enough a character)
Strong Bad/Homestar Runner
They'd be great all in the same poker game together but only the following strike me as worthy additions:
King of Town
Pompom
Team Fortress
I don't know the franchise at all so this is a pure guess
Spy
Penny Arcade
Gabe (could be hilarious, especially in interactions with Morgan Le Flay)
Monkey Island
X Guybrush (he'd think his strategy aloud and inadvertently tell everyone his hand)
X Elaine (not complex or funny enough character)
Voodoo Lady (a bit monotonous and predictable but could also be very funny)
LeChuck (strong and sneaky, aka someone Heavy would look up to, as well as being very funny)
X Stan (not suited to the setting, at all)
Herman Toothrot (maybe only because he's funny and we'd see some character development)
Morgan (would be the female, schoolgirl aggressive version of Tycho, someone for Gabe to wind up)
Wallace & Gromit
X Wallace (too boring and predictable)
X Gromit (brilliant faces but wouldn't be able to take part in conversations)
X Penguin/Chicken (see above)
X Cooker (see above)
X Preston (see above)
X All Wallace's former love interests (not fitting to the situation)
Bone
X Fone (too much of a one-dimensional character)
X Phoney (see above)
X Smiley (see above)
X Thorn (see above)
Rose
X Dragon (wouldn't fit in the shot very well)
Puzzle Agent
X Nelson (his personality would be too flat in a scenario like this)
Back to the Future
X Marty (similar in personality for this setting as Tycho Brahe, Fone Bone and Nelson Tethers)
X Doc Brown (a mad-but-good scientist stereotype would not fit this game if we're still playing poker)
Biff (could be rather like Strong Bad but in hard mode, would have the Armanak with him so would be like Max with Futurevision(tm))
Jurassic Park
Nobody would be suitable.
Not followed CSI or Telltale Texas Hold-em at all so cant comment on those.
Bah, Ian Malcolm would be a GREAT poker opponent. Well, an entertaining one, anyway.
You only say that cause he's 2-dimensional.
Very funny but you could apply that to all the Homestar Runner and Penny Arcade characters, many whom I'd like to see/enjoyed seeing in Poker Night at the Inventory.
Sam & Max: Sam and Flint Paper.
SBCG4AP: Homestar and The Cheat
Team Fortress 2: Spy and Sniper
Penny Arcade: Gabe and Annarchy
These would be awsome
Duke Nukem, Earthworm Jim, Clank, Daxter, Conker, The Tick, Wario, Scout, Leisure Suit Larry, Manuel "Manny" Calavera
Wheatly would also be funny but idk how he can play cards anyway o.o
Still a DLC would be epic for Poker Night, Valve could support hopefully with extra items for Portal and TF2 again since they love indies.
It would be nice to have some of them, but I don't think Telltale would have the time or patience to secure the necessary rights to those characters, with the notable exception of Scout, who could actually get in the game considering that Telltale has previously cooperated with Valve for Poker Night and TF2.
Sidekick Night
Guybrush and Murray
Papierwaite and Norrington
Strong Mad and The Cheat
Wallace and Gromit
Homestar Night with Subtitles
Pom Pom
Homsar
The Cheat
Poopsmith
For fully balanced configurations, I'm working on an extensive list, which I shall upload when I'm done for scrutiny and ever-coveted internet points.