This is my favorite show of all time. So I am biased, what can I say.
The characters and situations contained in this lovely sitcom still resonate with contemporary concerns while remaining a time capsule of the late 1950's.
Of course the standout element is Maynard G. Krebs- the primary supporting character portrayed by Bob Denver. Krebs is a beatnik and his endearing qualities include his immense loyalty to Dobie and his fearless determination to follow his own drummer, however odd it may seem to the rest of the world. Maynard is my personal hero.
The second standout character is the wonderful Herbert T. Gillis, Dobie's father played with great élan by Frank Faylen. Frank was a vaudeville veteran and clearly relished his role and often stole scenes from the rest of the cast.
Dwayne Hickman was wonderful and charming as the young Dobie, but his performances became scattershot as the series progressed and his appearance changed dramatically. He gains weight, his hair darkens, and he looks like he's aged 15 years from the beginning of the series to the end.
Florida Friebus does a wonderful job as Dobie's mother Winnie as well.
Perhaps the most unusual character after Maynard has to be that of Zelda Gilroy- the mousey, homely girl who loves Dobie as much as he loves every OTHER girl in town. Played with wonderful verisimilitude by Sheila James.
The rest of the cast is generally above average as well. Much has been written about Tuesday Weld, and deservedly so. She positively glows. Future luminaries such as Warren Beatty, Yvonne Craig and a young Ron Howard also appear. There is also a wonderful cast of stock and character actors who many viewers will recognize from other shows such as Mel Blanc, Doris Packer, Jean Byron, William Schallert, and Steve Franken.
The best episodes have a wonderful core of realism to them addressing some genuine concern of a teenager of that (or any) time. Be it money, dating, friendship, loyalty, family, greed, temptation, etc. The sometimes absurd plots are always centered upon the character’s relationships with one another.
Even the most outlandish and poorly written episodes (and there are some) usually contain good performances from the cast and interesting interactions from them. As stated above Denver and Faylen both excel in this, often making a mediocre scene quite enjoyable and a good scene an absolute riot.
There is a wonderful sense of an era frozen in amber to the series, and in many ways it is the prototype for "Pleasantville" as much or more than The Andy Griffith Show or Leave It To Beaver or any of the other shows one generally thinks of.
It might just be when I first saw the show, as an awkward teenager in the mid 80's, but The Many Loves of Dobie Gillis changed my life, and in many ways saved it. I really learned all I need to know from Maynard- be yourself, be loyal, and be sincere.
I would recommend the series to anyone who is a teenager, a fan of teen comedies, the 1950’s, television history, or Bob Denver.