In 1956 the legendary Boston pol and convicted felon James Michael Curley was immortalized in Edwin O'Connor's "The Last Hurrah," a thinly veiled fictional account of the final campaign of the wily city boss.

Now, 42 years, two Kennedys and one Tip later comes another Irish Catholic former mayor of Boston in a saga that might well be titled "Ray's Last Hurrah."

Raymond L. Flynn, the pub-crawling former college basketball star who left the mayor's office five years ago for a checkered stint as ambassador to the Vatican, wants back into the political game in the worst way.

Although he has had his ethical scrapes, Flynn's no felon, nor does he have Curley's sharp wit. But the 59-year-old Flynn shares certain traits with the man who served four terms as mayor, one as governor and four as congressman in the district Flynn now hopes to represent.

Both men were feisty raconteurs; both were unafraid to use their ethnic heritage, sometimes as club, sometimes as crutch. Both had a gift for the personal touch and, like Curley four decades before him, Flynn seems constitutionally incapable of giving up the political life.

"I didn't want to walk away from what I love doing," the ruddy-faced Flynn explains during a brief pause in his peripatetic campaigning.

He flirted with the governor's race, but the prospects for an out-of-office, cash-strapped, antiabortion candidate looked bleak. So when Rep. Joseph Kennedy II announced his retirement citing family problems, Flynn leapt at the chance to run in the 8th, a compact urban district with a past as storied as his own.

These days, the man who once presided over parties in the opulent mayor's mansion on Beacon Hill now drives the streets of Boston in a rented four-wheel-drive, searching for friendly faces.

To a lone black man perched on a bench, he says simply, "Hey brother, how's it going?" In a sandwich shop nearby he signs an autograph for a young woman and pleads with her to return to college. And at a cookout sponsored by the local Veterans Benefits Clearinghouse, he hugs Doris Graham, a community activist who fondly remembers Flynn's heyday.

His campaign pitch is summed up in an ad in the East Boston paper: "Ray Flynn has been there for Eastie . . . Parks, Fire Stations, Police Stations, Libraries, Elderly Housing, Youth Programs."

Yet in this era of "third way," suburban, New Democrat politics, Flynn's New Deal, patronage-oriented, urban populism may have outgrown its welcome even here in the bosom of liberalism. The triple-decker houses once bulging with large ethnic families are now occupied by yuppies for whom the name Flynn is just a distant memory.

While some candidates attempt to repackage themselves or tack with the political winds, Flynn is adamantly retro -- hoping the style and themes that worked so well nearly two decades ago can deliver one more victory.

As candidates all around him woo soccer moms, Flynn focuses on the downtrodden. While others race to slash taxes, he burns with the desire to convince voters that their tax dollars should be spent on starving children in war-torn foreign lands. And at a time when the standard House candidate spends $1 million on consultants, polls and television ads, Flynn wages his campaign with the ancient tools of political combat -- painted signs, free ice cream and his bevy of six kids.

"The 8th District fits me like a glove," Flynn contends. "It's a district that is philosophically and politically compatible with the values, concerns, issues and priorities that I have."

In reality, this son of a longshoreman and cleaning woman was all but compelled to run for the open House seat. He has never held a private-sector job and never drifted far from the spotlight, whether it was reaching crime scenes before his own squad cars or holding an umbrella for Pope John Paul II as the pontiff arrived in Denver in 1993.

It is all he knows.

For Flynn, the chance to assume the congressional mantle of Curley, Tip O'Neill and both Jack and Joe Kennedy would cap a remarkable 30-year career, begun in the bitter days of forced busing, tarnished in later years by a scathing newspaper account of his spotty performance as ambassador and his reputation for enjoying a shot and a beer.

On this particular summer day, Flynn's quest for one more office, one final hurrah, has taken him to Holgate Apartments, an elderly housing complex in the predominantly black neighborhood of Dorchester. Many of the seniors arrive in the sweltering community room gripping tattered photos of themselves with the man they alternately address as "Ray," "Mr. Flynn" and "Mistah Mayuh."

Flynn, whose typical campaign day begins with a 10-mile run and ends 18 hours later working the phone bank at a local union hall, has sweat stains under the arms of his gray suit.

The gathering resembles a reunion more than a campaign stop. Flynn's four daughters distribute free ice cream. The residents applaud Nancy Flynn's birthday and Julie Flynn's impending nuptials. Their father gives brief remarks, explaining why he chose the House race over the governor's contest and offering a quick catalogue of his accomplishments as mayor (better parks, more affordable housing, plowed streets and, he contends, racial harmony).

Meet Reginald Thomson, someone says to Flynn. He's a singer.

A singer? Flynn asks. Then, unprompted, Flynn begins to croon: "It had to be you. It had to be you."

Thomson, 77, joins in, the two unlikely voices hesitantly blending:

I wandered around

And finally found

Somebody who

Could make me be true

Could make me be blue

Or even be glad just to be sad

Thinking of you . . .

Stretching from leafy Belmont to scruffy East Boston, the 8th District is one of the last bastions of liberalism, a mix of highly educated professionals and blue-collar laborers unified by their Democratic politics. Just as this area was once the landing pad for Irish and Italian immigrants, today Armenians, Haitians and Puerto Ricans reside in communities such as Watertown, Chelsea and Somerville as well as throughout Boston and Cambridge.

Half the votes in the 8th come from the city Flynn ran for 10 years, and polls show him with a comfortable lead. So there is reason to believe he can corral the 20 percent probably needed to defeat the other nine candidates in the Sept. 15 Democratic primary and hence win a seat in Congress.

But as Flynn confesses to a supporter at Holgate, he no longer has the finely tuned machine that brought him 70 percent margins throughout the '80s. So Flynn has come calling on a powerful group of bosses, the 16 men who head Boston's building trades unions.

"It was not polls or money that got me where I am," he tells the group assembled at the local International Brotherhood of Electrical Workers. "It was the hard-working men and women of this city."

"We've always endorsed Ray," says IBEW business agent Michael Monahan. "He's never been afraid of taking an unpopular position for working people."

Look around Boston today, Monahan and others say, and you will see the city Flynn built: a new harbor tunnel, the Fleet Center, the Central Artery. By their math, 41 percent more labor jobs thanks to Flynn.

Flynn acknowledges what everyone in the room has been whispering: Several of his opponents are already on television, threatening to drown out his low-budget operation.

"They may have high-tech and different ways of reaching people, but if you can go out and hammer home the message of good jobs, education, the environment . . . this election can be won on the streets and in the neighborhoods," he says.

And that is why he needs them to send the checks, make the calls and yes, stand on street corners with his Kelly green signs. "I'd rather stand with you in hard hat and boots and lumberjack shirt than be on television spending $3 million on some slick political advertisements."

Flynn recounts a tale he heard from former House speaker John McCormack of Massachusetts. There once was a poor charwoman who pleaded with McCormack for a slot in public housing. He agreed, she got back on her feet and showed up at his office a few years later offering $10 for his next campaign. McCormack's aide refused the money, figuring the woman needed it more than the powerful speaker.

McCormack emerged from behind his office door, according to Flynn, and said, " If somebody wants to give $10 or $5 or $1, you take it because then that person is invested in your campaign.' "

"You get me $1, just $1," Flynn pleads with the men in shirt-sleeves. "I'll send that person a letter and we'll have the family forever."

Just across the highway, in Flynn's home turf of South Boston, union boss Tommy McIntyre is in his "office," a corner booth at Amrhein's restaurant and bar.

Though smaller, McIntyre is a Tip O'Neill look-alike, bulbous nose, sparkly eyes and all. Like the other labor leaders he has been with Flynn "a thousand years." But this time he's backing Susan Tracy, a Flynn protege who lined up the endorsement before Flynn entered the race.

"Those things happen in politics," McIntyre says with a shrug.

Back at the IBEW, Joe Nigro acknowledges that the old Flynn network has disbanded. "Political people go on to other candidates," he says. "But in their hearts, they're still with Ray."

Some others I've seen

Might never be mean

Might never be cross

Or try to be boss

But they wouldn't do

When Bill Clinton became president, Ray Flynn had big dreams. Secretary of housing and urban development, he figured, as a reward for his loyal service during the '92 campaign. His consolation prize was the Vatican, a largely ceremonial assignment but one the State Department views as a critical listening post.

From the outset, the skills that made him a beloved mayor clashed with the button-down, follow-the-rules, mind-your-p's-and-q's diplomatic world. He complained he wasn't paid enough, used embassy phones to make personal calls and more than once publicly contradicted the president, most notably when he sided with the Catholic Church on the question of abortion.

And just as he sprinted from fire engine to snowplow in Boston, jumping before the cameras in the heat of every crisis, Flynn sped around the globe venturing far beyond the Rome city limits. In Washington, news of his freelancing raised eyebrows. Today, his exploits have become his stock in trade on the campaign trail.

"No sooner was I on my job at the Vatican when I was instructed by the president to head up the American effort for humanitarian aid in India after the earthquake," he tells 1,500 members of the Ancient Order of Hibernians, the Irish Catholic civic organization.

Somalia, Uganda, Rwanda, Bosnia: Wherever there were people in need, Flynn says, he was there. "This is what our mission must be -- to reach out to those people who are without power, who are without voice, who are without influence, and we must be their voice."

Before Flynn's time at the Vatican expired, his hometown paper, the Boston Globe, greeted him with a brutal front-page article headlined: "Flynn at the Vatican: His Mayoral Style Didn't Cut It." At great length, the article detailed his rocky tenure in Rome, criticizing him for ignoring protocol, playing hooky his final year on the job and snubbing important diplomats.

Most damning of all, the 5,000-word story characterized Flynn as a "boozer," in the words of former mayor Kevin White, pointedly describing an encounter on a city street between a Globe editor and an obviously inebriated Flynn.

Today, Flynn is philosophical about the episode.

"I didn't want any fight with the Boston Globe," he says in an interview. "I just wanted to take the hit, move on. That's the way it is."

But when the story ran last October, Flynn responded in Curleyesque fashion, accusing the paper of an anti-Irish, anti-Catholic bias. The controversy dominated the Boston airwaves and prompted more than 200 mostly angry phone calls to the paper.

In the spring, Flynn got his revenge: A "60 Minutes" report accusing the Globe of moving the "scuttlebutt from the gossip page to the front page." He even invited the camera crew to his favorite watering hole, JJ Foley's.

"I'm here with friends, working-class people," Flynn says into the camera. "These are the salt of the earth."

It remains difficult to assess the impact of the story, criticized by some for failing to prove that his drinking affected his job performance but praised by many for finally letting a poorly kept secret out of the closet.

At a free evening concert on City Hall Plaza, passersby are asked about the prospect of Congressman Ray Flynn.

Some criticize his drinking. But Benjamin Rigsley worships Flynn and detests the Globe.

"He's a people's politician, not a politician's politician," says Rigsley, 59. As for the pub-crawling, "that's where you communicate, it doesn't mean he's a drunk. You ever been to Ireland? People sip two drinks all night, sit, talk and have fun."

Flynn's detractors -- and even some friends -- find much to criticize: He opposes abortion rights in an ardently pro-choice region; he is of the past and the race is "about the future," as Tracy puts it, or as another opponent, Chris Gabrieli, suggests, Flynn worries about dividing the pie, whereas Gabrieli wants to expand it.

Several candidates will outspend him and some, such as Somerville Mayor Michael Capuano, command solid voting blocs of their own.

The comparisons to Curley, the rascal charmer, should not be exaggerated. But like their heritage, their mesmerizing hold on their most loyal followers and their willingness to exploit ethnic tension, Curley and Flynn share one other trait: for pure entertainment, they will not disappoint.

For nobody else gave me a thrill

With all of your faults

I love you still

It had to be you

Wonderful you

It had to be you. CAPTION: Flynn at a cookout in an Italian neighborhood in East Boston: As his opponents woo the yuppies, Ray Flynn focuses on the downtrodden. CAPTION: In Rome, Flynn embraces Archbishop John Patrick Foley as he says farewell to the Vatican at the end of his stint as U.S. ambassador. CAPTION: Former Boston mayor Ray Flynn, left, sings along with Bill Kerns during an East Boston cookout. Flynn has moved here in his bid to win the 8th District. CAPTION: Flynn announcing his candidacy. "I didn't want to walk away from what I love doing," he said recently.