This is based on opinion. Please don't list it on a work's trope example list.
Tear Jerker / Phoenix Nights
The courtroom scene in Episode 7 is one of these. Jerkass though he is, there's something tragic about seeing Brian's downfall. He hasn't just lost his club, he's lost everything - his wage, his legacy, his circle of friends - all because Den Perry set his club on fire.
The ending to episode 4. After meeting the person he thinks is his true love, Brian dumps her on realising she was sent to investigate his (possibly) fraudulent disability claims. She's distraught, and keeps trying to contact him but Brian is having none of it.