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I found this form I'm not sure about:

少なくとも最後の最後、ばあさんはいいやつに会ったんだ。それで、きもちのいい運転でドライブを楽しんだ。車に乗ってるあいだは、楽しかったろう

The character is speaking about an old woman who, after taking a taxi, killed herself; the recipient of this sentence is that taxi's driver.

Does this 「たろう」 have the same meaning (or similiar) as 「だろう」? To be sure I I checked if past + だろう (「ただろう」) is a thing, and according to this page it is; I found this question about a similar form, but I don't think is the same, since to me my example seems clearly a past + ろう structure, while that case isn't.

(I didn't read accurately all the japanese citation in that answer, since I was having trouble understanding them; sorry if the answer is already in there.)

Edit: I just found this question, it does seem to be the same case.

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    This is not a question of たろう vs. だろう because the た in たろう is part of 楽しかっ. – l'électeur Dec 23 '19 at 13:50
  • That's what I meant with past + ろう, sorry if I wasn't clear; my understading - but I'm not sure about it - is that 「楽しかったろう」 is 「楽しかった」 + 「ろう」, and that it roughly has the same meaning as 「楽しかっただろう」. I edited the title hoping it's clearer. – Mauro Dec 23 '19 at 13:57
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少なくとも最後の最後、ばあさんはいいやつに会ったんだ。それで、きもちのいい運転でドライブを楽しんだ。車に乗ってるあいだは、楽しかったろう。

「ろ/ろう」 is an informal/colloquial sentence-ender expressing conjecture. It is used mostly by male speakers (and it does in fact sound quite masculine).

The phrase 「ばあさんはいいやつに会ったんだ」 is already quite colloquial and masculine, so 「ろ/ろう」 fits right in.

「ろ/ろう」 can be replaced by 「だろう」 or 「ことだろう」 for the basic meaning, but it will surely raise the formality level so I would not call those 'interchangeable' exactly.

In my personal experience, if that counts, I hear this 「ろ/ろう」 more often in Tokyo than in Nagoya -- the two cities I have so far lived my life in.

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明鏡国語辞典 第二版 has a dedicated entry for this たろう:

たろ‐・う

① 過去の事柄や完了した事柄についての推量を表す。~ただろう。「寒かっ━ね」「知っていれば来なかっ━」

②《多く上昇調のイントネーションを伴って》過去の事柄や完了した事柄について相手が同意することを期待しながら確認する意を表す。~ただろう。「君に見せ━?」「おもしろかっ━?」「僕が入院したことがあっ━、高校生のころ」

過去の助動詞「た」の未然形+推量の助動詞「う」。

活用語の連用形に付く。ガ・ナ・バ・マ行の五段動詞に付くときは濁音化して「だろう」となる。「君はもうこの小説を読んだろう」

Etymologically, it's analyzed as たろ + う rather than た + ろ(う). たろ is the "irrealis" (未然形) form of past-た (yes た can conjugate), and う is the particle for volition/inference. That said, たろう works as a set, and that's why this entry exists.

たろう is not particularly dialectal, but tends to sound old-fashioned if used in essays or novels (it's not archaic but smells like early-Showa or Taisho to me). It is still sometimes used in masculine colloquial speech today, in which case たろう is often contracted to たろ, and typically used with an accusatory overtone (for example 前にも言ったろ! = I said it before!).

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