Dinner at Mom's (Situational Irony)
The late-night supper at the home of Tommy’s mother has a heartwarming quality to it. We see Tommy in a new light, a doting son reunited with his adoring mother. The irony is, however, that Henry, Tommy, and Jimmy are on their way to dispose of the body of Billy, a prominent made man who Tommy killed viciously only a few hours ago. His shirt stained with Billy's blood, Tommy sits down to dinner, smiling at his mother and laughing at her jokes affectionately. The dissonance between the two sides of Tommy, one a cold-blooded killer and the other a juvenile mama's boy, is ironic. We do not expect a man so vicious and violent as Tommy to be capable of love, but in fact, he has a very loving relationship with his family. Thus, our subverted expectations create an ironic twist.
Dinner in Prison (Situational Irony)
Many of the sequences involving food are ironic, as when Henry is sentenced to ten years in prison and becomes a courteous chef. The viewer expects Henry and Paulie's incarceration to appear stark, Spartan, and difficult, a huge decline in their quality of life. Because they pay off and bribe the prison guards, however, their lives become almost utopian, each of them taking turns making dinner and pouring the wine, before sitting down to a lovely meal. The image of a bunch of grown men making dinner in prison is ironic firstly because we do not expect such brutish men to have such particular standards about food, and secondly because we do not expect them to be able to maintain those standards while incarcerated. Scorsese frames the short prison section of the film as if it were the opening sequence to a heartwarming home-for-Christmas movie. No iron bars, no striped uniforms, no cops. Jail, an institution built around deprivation, is a place of abundance for the mafia men.
Tommy's Death (Dramatic Irony)
This dramatic irony is sudden and quick. When Tommy goes to become a "made man," we see him being brought into a house for his ceremony, but something seems awry. As the Lucchese elders escort him into a mysterious room, the viewer can tell that he is about to get whacked, but up until the very last second, Tommy is preparing himself for the ceremony. In that brief moment when we realize that he is a dead man, the audience knows more than him, creating a tension. The dramatic irony is that we can see that Tommy's a dead man before he can.
Henry's perception of life vs. how we see it (Situational Irony)
Much of the narration in the film is in ironic juxtaposition with what we the viewer actually see onscreen. This disconnect cements the notion that life on the inside of any subculture creates its own perception of reality, creating for its participants a “new normal." Henry's ongoing description of his life as something akin to glamorous and enviable celebrity is often out of sync with the tawdry reality of his daily dealings. This creates an ironic distortion and detachment between reality and fantasy. There are countless examples of this, including the first voiceover monologue, in which Henry discusses his lifelong dream of becoming a gangster. He tells us that he always wanted to join the mob, and this admission comes immediately after we see a mangled body repeatedly stabbed and shot to death. Why anyone would want to join an organization that subjected him to such gruesome realities is hard to understand, and the contrast between his confidence in his decision and the viewer's expectation creates an ironic tension.
The Schnook (dramatic irony)
The film ends on the note of Henry regretting having to leave the gangster life to go into witness protection because his life is no longer what it was. And yet his biggest complaint seems to be that outside the milieu of New York Italian-American organized crime he can’t find a decent place to get Italian food. His life now is self-described as one in which he has become a schnook; Yiddish slang for a dupe who is easily bamboozled. The irony cuts especially deep, of course, because Henry is a schnook for buying into the mobster mythos in the first place.