How to help the player, play a cool character

roleplaying

Similar to a previous question about playing smarter characters I'm looking for techniques and strategies for playing badass characters that are a lot cooler than me.

Specifically I'm asking for a player, Bob, in my group, that likes to play badass military type veterans in the vein of movie action heroes. The group is fine with this and we play games that allow for this kind of characters.

The Problem

Bob quickly becomes flustered if confronted or a situation arises where his character could shine. Even when the confrontation is not direct, or there is no real live time limit on his action.

Especially after something like that happened he also starts to wildy change the way he plays his character. Becoming a "model soldier", when previously describing his character as a rough veteran, that only cares about results.

All of this leads to him making decisions that make his character look stupid. This leads to the player becoming frustrated. Other player characters acting on this behaviour will make that frustration obviously worse.

He then quickly begins to take things personally, which is understandable. The other players would like to help him, but are unsure on how to do it. They also often stop engaging with his character if there is a chance of him taking this personally.

The Question

As we are a group of friends, we are invested in his fun.

How can we, as a group, help Bob to play his character more consistently the cool, badass character he wants to play?

Some Examples

Tactical play example

Me, the GM, narrates an encounter in a Star Wars game: Your rebel team is suddenly surrounded by a group of bounty, coming out of the
jungle. The heavily armored Trandoshan with a grenade launcher, you
fought a couple of sessions back, steps out of the shadows.

Bob sits straight up, barking orders, before I can even ask for initiative:* Everyone! Come here! Stand together back-to-back!
Charlie looks confused to him: Dude, that's the guy that almost killed us in the spaceport.
Bob: Do it already, we are surrounded.
Charlie: Whose side are you on? You got that he still has the grenade launcher, right?
Bob realises his mistake and goes silent for the rest of the encounter.

Playing together

Bob's and Alice's rebel agents are sneaking through an imperial base, when they are surprised by an officer in an elevator.
Alice attacks the officer with a stun baton, almost dropping him (He is just barely able to stand). Bob uses his turn to draw his heavy rotating blaster rifle and shoots the officer. Even after being told that this is extremely dangerous and he could just draw his vibroknife, which would be quieter and would have no danger of hitting Alice's agent.

His roll goes badly and he actually hits Alice's Character for massive damage, almost killing her. When they are rescued from the rooftops Alice, as the agent, quips about him being a greater danger than the imperials.
Bob, the player, complains that everyone is against him.

Changing his character mid-scene

Bob's rough veteran sits in the briefing room with his feet on a table, when Alice's character, their commanding officer, comes in.

Alice states colloquially "This isn't your living room." and push his
feet off the table. She makes no indication that her character would
use any other tone. Bob immediately answers with a snapped "Sir, Yes,
Sir!", startling everyone at the table. We were confused as to whether
this was meant sarcastically by his character, but according to Bob
this was completely honest as his character follows orders and rules
as a good soldier.

I think everyone expected him to quip something like "Yes, Dad" back, as he had described the character as "a rough veteran, that cares more about results, than rank" and no one else in the group ever used "Sir" more than in passing. Also I think that he mostly described his character having his feet on the table to show how little he cares about decorum.

Best Answer

Simulationistic games can prevent unsuited roles

If a game is very simulationistic, it will be impossible to play a role where your character is supposed to be better at utilizing the rules of the game world than you are. Imagine a new D&D player going for a "tactical genius" character without understanding perhaps even their own build properly - it will not work.

DM: "You realize you are surrounded by the bounties you were looking for. The Trandoshan you fought previously steps out from the shadows, brandishing their grenade launcher."

Bob: "Everyone! Come here! Stand together back-to-back!"

DM: "Roll for initative."

<rolls>

DM: "The Trandoshan wins initiative and fires the grenade launcher into the middle of your group, killing everyone, campaign over."

A narrativistic approach is helpful, here; the simulation isn't as firm and can be altered as needed for the narrative. The GM is, in general, supposed to be less "impartial arbiter" and more "story cohesion guide". The player wanting to play a "tactical genius" could either be fed ideas by the GM, or their seemingly bad ideas could be re-spun as "genius beyond the superficial".

GM: "You realize you are surrounded by the bounties you were looking for. The Trandoshan you fought previously steps out from the shadows, brandishing their grenade launcher."

Bob: "Everyone! Come here! Stand together back-to-back!"

GM: "You swiftly bring the group close together, then suddenly grab your NPC guide, holding them as hostage against their spouse, the Trandoshan, who dares not fire their grenade launcher and orders the bounties to stand down."

Bob: "...just as I planned."

Charlie's attitude needs an adjustment

If Bob is supposed to be a competent veteran, Charlie's player should not be taking out their frustrations with Bob's player on Bob. Instead of talking down to Bob, "Whose side are you on", Charlie should be treating Bob as knowledgeable.

"What? But won't the Trandoshan be able to take advantage of a tight formation with the grenade launcher? Do you know something I don't?"

Charlie's player should give Bob's player and/or the GM a chance to retcon WHY a tight grouping will be effective. Or perhaps even attempt to brainstorm one.

Alice's player needs to chill

Bob becomes quickly flustered, yet after a poor roll, Alice chooses to have their character hold it against him. Bob's character was clearly trying to assist, and is supposed to be good at it, but something went wrong - does it make sense to take a jab at the player actually trying a decent strategy?

The GM needs to take responsibility

I'm not seeing any support for Bob in your examples. In fact, I pretty much agree with his statement that everyone is against him. It feels as though the group, including the GM, has decided that he and his characterization is a problem, instead of trying to support him.

You describe a grizzled veteran reacting to a reprimand from a superior officer with a "Sir, Yes, Sir!" as "changing his character mid-scene". Either I am missing a lot of context, or this seems a perfectly reasonable reaction. Were you expecting a "nor is it yours, so chill"?

When Bob had bad luck with his dice and the critical failure table happened, you could have described the events in any way you chose. The important part was that Alice would end up taking damage from Bob's rifle due to the fumble, which could easily have been described as something like:

GM: "As you draw your rifle, the officer grabs Alice's wrist. Unwilling to risk hurting Alice, you use the butt of your gun to shove him away from her - however, in his flailing he grabs your trigger and your gun discharges into Alice!"

Similarly, when Charlie dismisses Bob's idea and reminds the table of the grenade launcher, you could have amended the situation:

GM: "<Bob's character> seems to have noticed a slight detail - the chamber of the grenade launcher is empty, as is the Trandoshan's bandolier. The Trandoshan is out of ammo, and was using the empty launcher to trick you into spreading out, making you easy pickings for the bounties!"

Basically, Bob needs support

Bob is in a situation which Bob isn't equipped to handle, and the rest of the table seem to have agreed on this and him being a problem, rather than providing him with narrative support.

He has realized the situation and is struggling to contribute, yet player characters (and possibly players and GM) keep arguing against, questioning and denigrating his choices and actions.

Help his character succeed with what he wants his character to do and be, don't force him to conform with your own ideas of what he should or shouldn't be.