Lido Shuffle

Lido missed the boat that day He left the shack But that was all he missed And he ain't comin' back

Others got this right: he missed his chance to live a clean life; but he was more than smart enough to embark on his tour de force...

The shack was in Los Angeles (actually, Inland Empire). He's driving out Highway 66.

At a tombstone bar In a juke joint car He made a stop

In a ratty jalopy/beaten-up car, he made a detour to Las Vegas. Boz was equating anything southwest with Tombstone, AZ

Just long enough To grab a handle off the top

One-armed bandit/slot machine. Anyway, the inference is he won, and left.

Next stop Chi town Lido put the money down Let 'em roll

Gambling's illegal in Chicago. It's the other end of Hwy 66, btw, from LA to Chicago, mostly gone now

He said one more job ought to get it One last shot 'fore we quit it One for the road

Very 70's attitude. The word 'job' here implies he's a burglar, as does 'hit' below

Lido Whoah oh oh oh He's for the money He's for the show Lido's waitin for the go

Lido Whoah oh oh oh oh oh He said one more job ought to get it One last shot 'fore we quit it One more for the road

Lido will be runnin' Havin' great big funnin' Till he got the note Sayin' tow the line or blow it And that was all he wrote

Okay, I actually think this is transcribed wrong. I think it's "Lido B. run, having great big fun..." but it doesn't mess with the meaning. He was making too much noise (law enforcement/FBI) for the local mob to want to deal, so they sent him a message... and he chose to leave rather than fight (he didn't miss that boat)

He'll be makin' like a bee line Headin' for the border line Goin' for broke Sayin' one more hit ought to do it This joint ain't nothin' to it One more for the road

Mexico... and he'll start a new life after the last hit (robbery). This joint has nothing for security, it's easily knocked-over.

Lido Woah oh oh oh He's for the money He's for the show Lido's waitin' for the go

"One for the money, two for the show, three to get ready and four to go". Show here means both third-place (first is 'win', the money; second is 'place', for less money, and third place is 'show', as in 'show in the standings'). It probably also means that he likes being flashy and a showoff.

Lido Woah oh oh oh oh oh oh One more job ought to get it One last shot then we quit it One more for the road

Lido Woah oh oh oh He's for the money He's for the show Lido's a waitin' for the go Lido Woah oh oh oh oh oh One more job ought to get it

Fun song, and I like singing it on roadtrips in the southwest.