So Robert De Niro walks into a bar…

"I've been working on this film for seven or eight years," says Robert De Niro, on the phone from New York to talk about his new film The Comedian. "We started it … different directors were brought in."

A comedy, The Comedian stars De Niro as an edgy stand-up struggling for second chances. The directors which De Niro (Bob – his assistant who puts the call through refers to him as Bob) doesn't name possibly include Mike Newell, Sean Penn and Martin Scorsese. (The latter, of course, directed De Niro as a comedian in the classic pitch-black 1982 film The King of Comedy.) In the end, Taylor Hackford held the megaphone for The Comedian.

"We arrived at where we arrived," De Niro says, probably shrugging on the other end of the line.

The old saying is that dying is easy, but comedy is hard. Making a good movie about comedy might be harder, and making a comedy about comedy might be even harder still.

A year ago, the Guardian polled 10 comedians to come up with a list of the 50 funniest films of all time. The list is eclectic – it didn't have me at Jerry Maguire – and included two films on comedy: The Aristocrats (Penn Jillette and Paul Provenza's excellent 2005 documentary on the many variations of a filthy vaudevillian joke) and, yes, The King of Comedy.

(De Niro, no stranger to comedies, also shows up in the list with the inclusion of 2000's Meet the Parents, a film that features the actor asking, "I have nipples, Greg, could you milk me?" in excellent straight-face.)

When it comes to films about comedians, the tendency is to go dark rather than aim for hilarity. Some are strong (Lenny, Man on the Moon, Funny People and Richard Pryor's Jo Jo Dancer, Your Life is Calling), while others are so-so (Punchline, with Tom Hanks and Sally Field).

Enough to say, then, that being funny about being funny is no laughing matter. In The Comedian, De Niro is the fictional Jackie Burke, a jokester who years after starring in a beloved sitcom is attempting to reinvent himself late in life. Nailing the character – "We wanted to get it as real as possible," says De Niro – was an exacting, back-and-forth process.

The film was the passion project of De Niro and Art Linson, one of the four people with screenwriting credits. One of the others is the insult comic Jeffrey Ross, who was brought on early in the writing process. In other interviews, Linson, a friend and colleague of De Niro's, has said that almost all of Ross's gags were eventually cut from the script. Apparently, his stuff was too edgy, so screenwriter and awards-show writer Lewis Friedman was brought in to soften De Niro's character a bit. Comedian Jim Norton had some input as well.

A few of the scenes were shot in the Comedy Cellar, a famed basement in Greenwich Village, where, just last month, Chris Rock took the stage, along with wisecrackers of note Jerry Seinfeld, Amy Schumer, Aziz Ansari and Dave Chappelle.

De Niro says that for a long time, he stayed away from comedy clubs, but in preparation for this role, he started dropping in on some of the New York venues. He caught Jessica Kirson (who, along with Norton, is one of the many comics in the film), and used her "inner monologue" bit for his flawed, foul-mouthed Jackie Burke.

Asked about his favourite joke makers, De Niro names Kirson, Chappelle, Don Rickles, Lenny Bruce, Bill Murray, Jack E. Leonard, Richard Pryor and Jim Belushi (a friend of his). Also on his list are Richard Belzer and Billy Crystal, both in the film.

"You can be given some freedom, in theory," the actor says, about stand-up comedy. "You're saying things that hopefully are funny and clever and make a point. It can be a hard thing to do."

A very hard thing to do. In The Comedian, De Niro's funny man is attempting to stay relevant. Jackie Burke is known for his old sitcom character and the guy's signature catchphrase. That his fans confuse him with his character is a source of frustration.

So, it's probably by design that Jimmie Walker appears in the film. Nearly 70 years old, Walker is forever linked to his "Dy-no-mite!"-saying character J.J. on the seventies comedy Good Times.

Of course, being remembered for one thing is better than not be remembered at all. "It's special to be recognized for something you did," the you-talkin'-to-me? actor says. "Even if it's for something you did once, most people don't get that."

Better to be king for a night than schmuck for a lifetime? "That's right," De Niro says quickly in agreement.

It's a great line, that one, about ruling if even just for a moment. Wish I could remember who said it.