I would put Robin: Flying Solo somewhere between Teen Titans: Child's Play and Plastic Man: Rubber Bandits in terms of darkness. This is the era of Tim Drake as Robin and takes place at the time of the Batman: Knightfall storyline. Here, Robin is on his own while Bruce Wayne is both recuperating and trying to find Tim's dad, who has been kidnapped. The main story involves a hunt for three escaped prisoners - Cluemaster, Electrocutioner and the newly named Headbanger. And it's not easy for Robin to do the search. He's got school to deal with, a girlfriend who doesn't know his true identity and is convinced he's cheating on her, a County Sheriff who thinks he's less than useless and Cluemaster's daughter, the Spoiler, all to contend with while trying to find out what these three are up to. Things, of course, have to break somewhere.
I really enjoyed reading this comic. I'm not as familiar with Tim Drake's Robin, so it was a nice introduction to his world. It had wonderfully written teen angst, with Tim unable to tell Adriana (his girlfriend) why he keeps breaking dates, having a foe in the local football hero and a bit of attraction between Robin and the Spoiler. It was a quick read and was another one that I didn't mind my 4 year old reading. He's definitely getting his grounding in the classics.