So Sidney braces himself and slinks into the dining room for an encounter (and the film's first look) with the beetle-browed, thick-spectacled, pallor-faced, power-mongering columnist J.J. Hunsecker (Burt Lancaster), who has commandered a table. In front of him are a telephone, sheets of paper, and pen - for note-taking and collecting items for his column. A steely, menacing and hulking presence with a skull-like, masked appearance to his face (due to his deepened eye sockets caused by shadows from his magnified lenses), he calls on familiar club personnel by name. Sidney deliberately positions himself at the elbow of Hunsecker, ready to dutifully deliver a message or respond to his beck-and-call. Crew-cutted Hunsecker half-turns, notices his lackey Falco, and then backhandedly insults the currying press agent with a comment to the Senator seated with him:

Harvey, I often wish I were deaf and wore a hearing aid. With a simple flick of the switch, I could shut out the greedy murmur of little men.

Falco gambles on a new tactic to gain Hunsecker's attention and remain in the columnist's hallowed presence - he tells Hunsecker that his sister's romance is more serious than previously thought: "I've got a message from your sister." Hunsecker's threatening tone is calmed, and Sidney is allowed to remain with J.J.'s other table guests:

• an angling politician-Senator Harvey Walker (William Forrest)
• show-biz hopeful Miss Linda James (Autumn Russell) - the Senator's call girl
• and her alleged agent-manager Manny Davis (Jay Adler)

In a curt phrase, Hunsecker sums up the entire trio of characters: "Everyone knows Manny Davis...except Mrs. Manny Davis." At his whim and will, Hunsecker casually accepts and rejects petitions of information for his column (his life-and-death, make it or break it judgments are regarded as "capital punishment" or as a death sentence by Sidney). Nothing has escaped Hunsecker's notice - he has seen through the sham of Manny Davis masquerading as the agent for "this lovely young thing," a singer with "Jersey City brains":

The brains may be Jersey City, but the clothes are Trainor-Norell.

When Linda calls Falco a pretty boy ("He's so pretty..."), Hunsecker delivers a brilliant, but vitriolic and foul monologue ending with the famous line ("Match me, Sidney"). He degrades Falco, describing him as more than just a pretty face with a grinning exterior - underneath he is a slimy, "hungry press agent," with a contemptuous streak, who changes his nature depending upon whose favors he needs:

Hunsecker: Mr. Falco, let it be said at once, is a man of forty faces, not one. None too pretty and all deceptive. You see that grin? That's the, uh, that's the charming street-urchin face. It's part of his helpless act. He throws himself upon your mercy. He's got a half-dozen faces for the ladies. But the one I like, the really cute one, is the quick, dependable chap - nothing he won't do for you in a pinch. So he says! Mr. Falco, whom I did not invite to sit at this table tonight, is a hungry press agent and fully up to all the tricks of his very slimy trade. (He turns with an unlit cigarette toward Sidney, gestures, and waits.) Match me, Sidney.
Sidney: Not right this minute, J.J.

Sidney is not up to compete against or (or "match") J.J.'s insults, so he declines to play the game and become subservient again - and light Hunsecker's cigarette, although his life's focus is on idealizing his foul mentor. After composing himself after the humiliating intimidation, Sidney answers the Senator's question about how a press agent works at the bidding of an enslaving, vicious newspaper columnist. However, he adds that there is a symbiotic relationship between publicity handymen and their assassinating publishers, although Hunsecker denies such a connection:

Sidney: A press agent eats a columnist's dirt and is expected to call it manna.
Senator: But don't you help columnists by furnishing them with items?
Sidney: Sure, the columnists can't do without us, except our good and great friend J.J. forgets to mention that. You see, we furnish him with items.
Hunsecker: What, some cheap, gruesome gags?
Sidney: You print 'em, don't ya?
Hunsecker: Yes, with your clients' names attached. That's the only reason the poor slobs pay you - to see their names in my column all over the world. Now, I make it out, you're doing me a favor?...The day I can't get along without a press agents' handouts, I'll close up shop and move to Alaska, lock, stock, and barrel.

The reptilian and malevolent Hunsecker takes another few career digs at press agents, thereby calling into question Manny's integrity. He insinuates and warns the wanna-be President that press agents often backstab public figures by publicizing scandals: "They dig up scandal about prominent people and shovel it thin among columnists who give them space." The Senator comments on Hunsecker's threatened tone:

Why is it that everything you say sounds like a threat?

Hunsecker replies that it is only a "mannerism" of his to appear dangerous and emphatically threatening, and then advises his Senator 'friend':

But why furnish your enemies with ammunition? You're a family man, Harvey, and some day, God-willing, you may want to be President. And here you are, out in the open, where any hep person knows that this one (the camera swings to pimp Manny) is toting that one (the camera swings wildly over to the blonde mistress) around for you (the camera moves to the Senator)! Are we kids, or what?

The occasion abruptly ends, with the guilty Senator humbled and properly chastened: "Thanks, J.J., for what I consider sound advice." Imperially, Hunsecker replies: "Go thou and sin no more." As he leaves the restaurant, Hunsecker instructs the captain: "Don't let the Senator pay that check." And then he sarcastically mutters under his breath to Sidney, who is like a lapdog following at his side:

President!...My big toe would make a better President.

At the checkroom, Hunsecker accepts his coat - without offering a tip! But almost immediately, as they ascend the steps from the basement club, he criticizes Falco for the same behavior:

Where's your coat, Sidney? Saving tips?

Sidney recognizes Hunsecker's "fat friend" - iron-fisted, corrupt police detective Harry Kello (Emile Meyer), who is sitting in a squad car across the rain-slickened street. In front of Schrafft's, the columnist shares small-talk with his favorite cops on the beat. They are indebted to him and worship him for his nepotism - providing additional sources for the city's happenings as repayment. Kello returns the insult toward Sidney for calling him J.J.'s fat friend: "I call him the boy with the ice-cream face." [This is one of many allusions made between people and food (often non-nutritional) within the film, including ice-cream, a barrel of pretzels, waffles with syrup, a tangerine that peels in a minute, a chicken in a pot, cookie full of arsenic, a bowl of fruit, etc.]

After Hunsecker and Sidney observe a drunk being thrown out of Club Pigalle into the street and kicked, Hunsecker turns and sadistically smiles with an exultant grin:

I love this dirty town.

He signals for his black Lincoln Continental limousine to pull up by the curb and linger conveniently closeby as he strolls along the sidewalk with Sidney. They discuss Hunsecker's hard-edged and malicious, over-protective concern, while Sidney attempts to regain the displeased columnist's good graces after failing to break up Susie's romance:

Hunsecker: Sidney, conjugate me a verb. For instance, to promise. You promised to break up that romance - when?
Sidney: You want something done, J.J., but I doubt if you yourself know what's involved.
Hunsecker: I'm a schoolboy - teach me, teach me.
Sidney: Why don't you break it up yourself? You know you could do it in a couple minutes flat.
Hunsecker: At this late date, you need explanations? Susie's all I got. Now she's growing up, I want my relationship with her to remain at least at par. I don't intend to do anything to antagonize her if I don't have to. Be warned, son, I'll have to blitz you.

Sidney vehemently complains that he doesn't like the job he's been given: "We've got a slippery, dangerous problem here." He decides to divulge how serious the couple have become - romantically - to the mean, morally-bankrupt columnist (who claims with a twisted reference to the Bible: "my right hand hasn't seen my left hand in thirty years"). And then Sidney pleads for more mentions in the column. During the bargaining session with the evil and omnipotent columnist (J.J. represents a God figure or 'father' to Sidney), Sidney receives tacit approval to carry out his secretive, 'uncharitable' deed/scam and 'deliver' - for later rewards given in secret (rewards of publicity):

Sidney: ...if I'm gonna go out on a limb for you, you gotta know what's involved.
Hunsecker: My right hand hasn't seen my left hand in thirty years. [Matthew 6:3, paraphrased: 'But when you do a charitable deed, do not let your left hand know what your right hand is doing, that your charitable deed may be in secret; and your Father who sees in secret will Himself reward you openly.']
Sidney: I'll do it, J.J., don't get me wrong - in for a penny, in for a pound. I'll go through with it. But stop beating me on the head. Let me make a living!
Hunsecker: Sidney, what you promised - do it! Don't finagle around. It's later than you think.
Sidney: Excuse me, J.J., it's later than you think. That boy proposed to her. (Hunsecker stops walking, pauses in the dark shadows, and ponders the weighty matter.)
Hunsecker: Susie told you that?
Sidney: Uh, huh.
Hunsecker: What was her answer?
Sidney: She'll discuss it with you at breakfast.
Hunsecker: That means you've got a plan. Can you deliver?
Sidney: Tonight, before you go to bed. The cat's in the bag and the bag's in the river.
Hunsecker: Don't be a two-time loser, Sidney. The penalty could be severe.

As Hunsecker's car pulls away into the black urban jungle, exhaust fumes spray out at Sidney's pant's leg. He brushes them away, smiles smugly, straightens his tie, and with an animated step proceeds to Toots Shor's Restaurant to speak to Leo Bartha (Lawrence Dobkin), Hunsecker's rival columnist.

Duplicating J.J.'s own strong-arm tactics, Sidney decides to blackmail Bartha over his recent proposition of Rita, and compel him to write a "dirty little smear item" in his column about Steve Dallas. The slander would break up the couple's planned betrothal. His first threatening words to Bartha reveal his sinister purpose:

How goes the Sunday piece on cigarette girls?

[A 'cigarette girl' represents a leggy, enticing glamour girl on display, while hawking a tray of goodies in a ritzy nightclub, who could casually trade her sexuality for favors, or become a mistress to a rich man if she wished.] Realizing that he is being blackmailed, in the presence of his wife Loretta (Lurene Tuttle), Leo is immediately antagonistic ("What is this, blackmail? Beat it!"). In a superb scene in a restaurant booth, Sidney drives a further wedge between Leo and his horse-race addicted, champagne-sipping wife (she calls her husband "Hitler!" at one point). When she surveys a cheap tabloid for a horse to bet on, the oily and repulsive press agent slyly asks:

Is there anything with a name like 'cigarette girl'?

Exasperated, Bartha refuses to let Sidney pressure him with blackmail any further: "This man is trying to hold a gun to my head," so he confesses and apologizes, with great embarrassment, to his wife for his foolish escapade (and exercise of "bad judgment" and "bad taste") with a "cigarette girl." And then the principled Bartha turns and rails at Sidney over his corrupt association with Hunsecker. He resolutely refuses to print the smear item:

Bartha: Your friend Hunsecker - you tell him for me - he's a disgrace to his profession. Never mind about my, my bilious private life. I run a decent, responsible column. That's the way it stays. Your man prints anything. He'll use any spice to pepper up his daily garbage. You tell him I said so. Tell him that like yourself, he's got the scruples of a guinea pig and the morals of a gangster.
Sidney: (sneering) What do I do now? Whistle 'Stars and Stripes Forever'?
Loretta: What you do now, Mr. Falco, is crow like a hen - you have just laid an egg. (To Leo, approvingly) Leo, this is the first clean thing I've seen you do in years.

From another booth in the restaurant, an onlooker has observed the entire altercation and outburst, and he asks a nearby waiter to summon Sidney. The witness is Otis Elwell (David White), another columnist from The Record, and Sidney haltingly approaches, fearing that the incident will be reported: "If you're trying to blow this brawl into an item for your column, forget it!" Without any reference to his use of blackmail, Sidney explains that he was desperate for a mention in Leo's column, after being 'shut-out' and "washed up" by J.J. Hunsecker ("I'm eating humble pie this month").

The womanizing Elwell, who has just lasciviously eyed the beautiful female form of a woman passing by and is browsing through SENSATION (a girly magazine), catches Sidney's attention and he develops another ploy. He presents Elwell with the Dallas smear item ("a fine, fat dirty item") on a slip of paper - the same one rejected by Bartha, while denouncing Hunsecker:

I make no brief about my bilious private life, but he's got the morals of a guinea pig and the scruples of a gangster.

[His insult isn't even original - it's the one given by Bartha a few minutes earlier.] To persuade the cautious columnist to print the item, Sidney exploits Elwell's prurient interest in women: "Suppose I introduce you to a lovely reason."