There are four major clues to help us out. 1) Tommy is in art school, 2) Sean is a high school dropout with a year and a half to go to get his diploma, 3) the Donnelly patriarch was killed ten years ago, and 4) Jenny's husband has been missing for five years. Based on clues #1,2, and 3, Tommy was originally estimated to be 21 years old and Sean 18 years old, since it's unclear how long it's been since he dropped out of school. Kevin is between Tommy and Sean, so he must be 19 or 20. There's no technical upper limit regarding Jimmy's age except for the flashback scenes that show him as a child, which gives us a basis for comparison with the other Donnellys. So we'll just go ahead and say he's 23. Since Jenny is Tommy's major love interest, she is assumed to be his age. The brothers' father died when Tommy, Kevin, and Sean were all children and Jimmy was an adolescent, so the estimated ages make sense here.
It's clue #4 that screws up this scenario entirely. In "The Black Drop," there is an extended flashback sequence that shows some period when Tommy and Jenny were dating. The scene depicts the end of Tommy and Jenny's relationship and Jenny subsequently being friendly with her future husband. Since in present time, we are told that Jenny's husband disappeared five years ago, let's say that this flashback occurred six years ago. By the initial calculations, Tommy and Jenny would have both been fifteen in this scene!
Do they look fifteen to you? That means Jenny would have gotten married at fifteen or sixteen years old! So let's revise the ages. We'll say Tommy is currently 23 (maybe he took a year or two off before starting art school?), making him a slightly more acceptable 17 years old in the flashback. Let's keep the assumption that Jimmy is two years older than Tommy and thus must be 25, and Jenny is Jimmy's age instead of Tommy's age. Therefore, she would have married at 19. We'll say that Kevin is currently 21 years old, which actually makes more sense than the original scenario since he's always shown drinking in bars. There's no real need to revise Sean's age. HOWEVER. We still have a problem. See, in the flashback, after Tommy confronts Jenny's dad (who, evidently following in the tradition of interfering Irish parents, wants Tommy to stop seeing Jenny), he then goes to the Firecracker Lounge to try to make things up with Jenny. There, he finds Jimmy, Kevin, and Sean. Jimmy tells him that he just won the Firecracker in a bet. It's a little hard to see in the screenshot below (the director never did fix the goddamn lighting), but all four brothers are clearly present.
If this happened six years ago when Tommy was 17, Jimmy would have been 19, Kevin would have been 15, and Sean would have been 12. Sean would have been 12. Forget the legal drinking age, Sean wouldn't even have reached puberty yet! And yet there they all are, drinking beers and looking exactly the same as they do in the present age. So unless the brothers magically skipped ten years of their lives, we kind of have a problem. Either the writers didn't notice this, or they were hoping we wouldn't notice.
I'm not demanding an explanation or revision, though. I think it's kind of perfect, actually, because it's so emblematic of the issues that plagued the entire series. On the one hand, they wanted The Black Donnellys to be serious, but in so many respects the characterization and plots they came up with just didn't convey much depth, and the dialogue (particularly between Tommy and Jenny) was too stilted. The writers did their best and I respect that, but it is what it is. And what it is kind of half-baked, but still entertaining in lots of unexpected ways. Even if that wasn't quite what they intended.
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