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Where the first season essentially followed the monster-of-the-week plus occasional storyline episode formula that has been tried and true on Buffy, Season 2 started to move away from that into the darker, emotionally churning state of being that we viewers have grown so used to in the third and fourth seasons.
The second season of Angel also points at the show's tendency to serve an overarching plot rather than a seasonal "Big Bad", when it ends with a trip to a different dimension instead of concluding the Darla storyline (which is completed in the third season).
But though this season has a darker, more plot-arc oriented spine, it still contains some excellent character and monster-of-the-week episodes. One of these is "Are You Now or Were You Ever?", thought by fans everywhere as being one of the best episodes of the show. Other greats include "Darla", "Guise will Beguise", and "The Shroud of Rahmon".
There are also portents of the futures of the different characters interspersed throughout the season. This is where Wesley really matured, becoming a hard-bitten leader rather than a comical sidekick. You can see his character being prepared to make the harder choices that cause him to be so dark later on in the series.
Angel himself has a hard time of it throughout this season, but then, when does he not? He grows dark, deep-set despair keeping him from both his mission and his friends. But his redemption is both funny and touching when he returns towards the end of the season.
Cordelia grows immensely during this season, primarily because of her visions. She's still "tell it like it is" Cordy, but her caring for others grows by leaps and bounds, setting the stage for the Cordelia we know later on in the third season.
Charles Gunn also joins the Fang Gang, forsaking his old 'crew' to help Angel Investigations in a slow process that is (fortunately) very believable.
Also in this season we are introduced to two new characters that will later become regulars: Fred and Lorne (the Host). The first is a slightly cooky, very intelligent woman who was stuck in Pylea for five years before returning with the Angel Investigations gang. The second, Lorne, is a truly unique character - a demon that sings, and can read a person's destiny when that person sings. Both are excellent additions to the group, and help to flesh out the dynamic between the characters.
In conclusion, Angel: Season 2 serves as a stage-setter for the third and fourth seasons' storylines and characters, and contains some truly memorable episodes as well.
However, the highlight of Season 2 is the Angel/Darla/Lindsey conflict, with the brilliant contributions of two gorgeous and remarkably talented actors, Julie Benz and Christian Kane. They were a devastating loss to the show when the storyline ended (although Benz makes a few appearances in Season 3 and one in Season 4). Drusilla enters in The Trial and, along with Stephanie Romanov (Lindsey's evil colleague Lilah), Sam Anderson (their boss Holland Manners), and Gerry Becker (his replacement Nathan Reed) provide the counterpoint to the Angel Investigations theme. These magnificent actors are gone from the show much too soon, with the exception of Romanov. And the storyline peaks in Reunion, an episode with an ending that must be seen to be believed.
Elisabeth Rohm (Kate Lockley) is another brilliant cast member who leaves the show at the end of this season, and Julia Lee (Anne Steele, who had called herself first Chanterelle and then Lily on two episodes of Buffy) appears too briefly.
Other highlights include songs by Andy Hallett (Lorne), Julie Benz, and Christian Kane, all of whom sing very well, and songs by David Boreanaz and the trio of Wes, Cordy, and Gunn, who don't! And the bookish Wes becomes a true hero as the season develops. In the last four (Pylea) episodes, he becomes a leader. There is also a very brief appearance by Eliza Dushku as Faith.
Buy this, watch this, and cherish this. You'll never see its like again. This is definitely the best of Angel.