"Whatever you are, be a good one." - Abraham Lincoln
Back when Batman was so badass that he seriously blew up a dude with dynamite, Bob served as the Joker's right-hand man as far back as the duo could remember. It is rumored that Bob was the one with Jack Napier that infamous Gotham night Thomas and Mrs. Wayne were murdered in the ally behind Gotham's Pearl and Phillips Street. Jack, ever a nutcase, came so close to murdering young Bruce Wayne he even asked his fatal question...
"You ever dance with the devil by the pale moonlight?"
Ever the yang to Napier's yin (or at the very least desperate to avoid capture for double-homicide), Bob convinced Jack to flee the scene, and thus spare young Bruce Wayne's life. (To this day he remains the only person to hear Jack's question, and live.) Thus the Wayne murderers got away, and Gotham's Caped Crusader was born... all because of the sensibility of one Bob the Goon.
The man who made the Batman.
The Goon was pretty good with a knife, well-respected by his peers, and loyally served as Napier's henchman until his horrific end at Axis Chemicals. When Jack Napier returned as the Joker, it was never a question where Bob's loyalties remained. Although working for a clown, Bob served as an effective surrogate to the Joker on the field without the slightest bit of makeup. He reorganized his men from goons to choreographed mimes in no time, and took such pride in his work that even his mere reconnaissance work looked worthy of National Geographic.
In addition to obtaining expert photographs in the time span of several seconds, Bob was also able to somehow learn both the name of the hottest girl in the crowd, Vicki Vale, and the man she was currently sleeping with: Bruce Wayne. Had Joker not grounded Bob with such mundane duties as fetching phonebooks and producing network-access cable TV commercials, Bob would have probably uncovered the Batman's secret identity simply from inspecting the guano on Miss Vale's beret.
Bob the Goon was a lowlife gangster to the core, but where here outclassed the big J was in the field of practicality. Jack Napier always was an "A-1 nutboy" who needed someone to keep him in line, and Bob was in a minority of one when it came to filling that post. And when you think about it, Joker was really more of an albatross than a leader to Bob throughout their entire career together. It is only because of some well-timed hostages Bob took (including Commission Gordon and Vicki Vale) that Joker's criminal empire was able to avoid the fate of so many lesser characters from Batman's rogues gallery.
Bob packed a mean kick, apparently.
From his humble beginnings to the bitter end, Bob the Goon simply could not lose his cool under pressure, and there is no better testament to this than two moments where he truly eclipsed his superior; Bob's finest moments. The first was when Batman held Jack Napier in his grasps, and the second was after Batman stole Joker's balloons loaded with Smilex gas. Bob handled both setbacks with calmness and composer, establishing himself as a role-model for any criminal in the DC universe. The Joker, on the other hand, got his face melted off despite Bob's insistence that they flee, and then vented his frustration over Batman's balloon-theft by shooting Bob, his best friend since middle-school, with Bob's own gun (which he handed to the Joker without hesitation.)
Loyal to the end.
If Bob the Goon had a failing, it was that he put his life in the hands of a sociopathic clown who thought that killing people was a freaking riot. To Bob, the Joker was always Jack Napier: A-1 nutboy extraordinaire who shared Bob's appreciation for the finer things in life, such as art. To the Joker, Bob was just a punchline waiting to go off.
Abraham Lincoln would have been proud of 'em both.
Bob the Goon (1947-1989)