Like most people, Colin was my favourite when I watched Press Gang as a kid. He's pretty high up when I watch it now too but, as jayson_firestorm points out, in some of the later episodes they milked his wackiness a bit and began to push out the shrewd businessman angle in favour of a loveable dunderhead character. This resulted in some hilarious scenes (including the infamous pet-killing scene from "Windfall") but had a negative effect on the character that Moffat and Paul Reynolds had built up in the earlier series. Still, our glimpse into Colin's more serious side in "Something Terrible" was one of the most brilliant pieces of character writing in the entire series as he struggled against the image he had created for himself in an attempt to convince everyone that he really needed help. The touching scene in which, confronted with the terrible truth Colin pleads "I can't cope with this" is a series highpoint.
As for jayson_firestorm's comments about liking Kenny being controversial, doesn't everyone love Kenny? I admit that when I was young I missed the subtleties of the character and only really remembered him for occasionally saying "bloody" on CITV, but watching the DVDs back I totally loved his character. A laid back Mr Nice who wants to please everybody and occasionally interjects with brilliantly witty lines that could even steal the thunder from Spike and Linda's quickfire banter. He was also brilliantly played by Lee Ross. I missed him during the final two series.
The other character that stood out after rewatching was Lynda. I never liked her much when I was young (except I had a small crush on Julia Sawahala) but now I've grown up I really appreciate her biting cruelty. As Steven Moffat himself says in one of the commentaries, she was the best character to write for because she could pretty much get away with anything since she was exactly as vile as she seemed to be. It's great to see a character like Lynda get away with immoral acts with absolutely no comeuppance(see the end of "Friends Like These" for a good example). Julia Sawahala got better at playing her with each series.
Worst character? It has to be Sarah (surprise suprise). I was never a fan of Kelda Holmes school play style of acting that sounded like she was just reading out the lines and Steven Moffat never seemed to know quite what to do with her. She got mostly serious story lines, although Moffat attempted to introduce a character trait involving her being unlucky with boyfriends which never really seemed convincing. It was sort of tacked onto her character in the later series. In most TV series with a lot of main characters, there is always one that the writer seems to struggle with more than the rest and Sarah was undoubtedly that character on Press Gang.
The other character that never worked for me was Julie but only in the last two series when she returned. She was fine in the first series as the airheaded girl from the graphics department, then she suddenly returned as a completely different character. The explanation for this is also given by Steven Moffat on a DVD commentary. When Lucy Benjamin was available to return and they needed a replacement for Lee Ross, Moffat simply threw all continuity out of the window and, by his own admission, gave Julie all of the character traits of Sam from series two.
Aside from those two characters, I also found Tiddler to be a bit dull mostly due to underdevelopment. She was virtually pushed out of the series as it went on and when Moffat tried to give her a lead story in 'The Week and Pizza', the result was one of the worst episodes of the lot.
Of those I haven't mentioned, Spike was obviously a strong character. His Groucho-style wisecracks were often inspired but sometimes annoying and I greatly preffered Spike as the series went on and his character was fleshed out and given real heart. He lost that slightly unconvincing "badboy" act after the first series and ended up being the main thrust behind many of the most moving storylines including "The Rest of My Life" and "Love and War". Dexter Fletcher still managed to give some great performances despite the dodgy American accent he was forced to attempt at the last minute and his accent actually improved throughout the 5 series. It also allowed Moffat to insert some hilarious in-jokes ("Don't worry Spike, we'll get a real American to play you" and "I thought you were from Birmingham").
Frazz worked best in the early series before his voice became deeper and he stopped really doing anything. The horoscopes schtik was great but it could only last so long and after that Moffat struggled to find storylines for the character, who was inexplicably promoted to having a picture on the title sequence despite having what was obviously a supporting role. The two Frazz episodes "Picking Up the Pieces" and "UnXpected" are both weak and Moffat seemed to lose sight of the original character he created, dropping the loveable half-wit angle in favour of a terminally apathetic non-entity.
Having said all that, I rarely find myself thinking "that character is so weak" when watching a Press Gang episode. The scripts and the cast generally carried the weaker aspects of the series and covered up the cracks brilliantly. Press Gang is the sort of sophisticated children's show we will probably never see the like of again; a brilliantly written comedy/drama that is just as enjoyable (if not more so) for adult audiences.
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