"try+ -ing form" V.S. "try+-infinitive"

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Could you please explain to me the difference between these two sentences?
- Joey tried to bribe the jailor.
- Joey tried bribing the jailor.

One more question: What's the difference between the following sentences?
- He starts to work at nine.
- He starts working at nine.
- He starts work at nine.

"Joey tried to bribe the jailor."
"Joey tried bribing the jailor."

The meaning is essentially the same. The second option would be better in some cases to avoid sounding redundant with the word "to."

For example:

"Joey tried bribing the jailor to get out of his cramped cell."

"Joey tried to bribe the jailor to get out of his cramped cell." (see what I mean)

"He starts to work at nine." (He begins working at nine, but he was not doing work before nine)

"He starts working at nine." (pretty much the same meaning as the first...relates to the other issue we discussed)

"He starts work at nine." (He begins working at his place of employment at nine).