Ashley Tisdale is going from High School Musical’s sharply dressed Sharpay Evans to the less clean-cut Emma Jean in her new role as a high-priced prostitute in the upcoming fifth season of FX’s Hamlet on a Harley drama Sons of Anarchy. Also joining Tisdale this year for a multi-episode story arc is Community star Joel McHale, who’s playing Warren, a handsome con man whose grifting ways put him into hot water with the wrong marks.

As previously mentioned, Tisdale’s saucy new character will be riding straight into trouble as the new SAMCRO president, Jackson “Jax” Teller (Charlie Hunnam), struggles with his leadership role while still trying to untangle friend from foe. In the premiere episode (titled “Sovereign”), fans will also be introduced to new character Nero Padilla (Jimmy Smits) – a Latino gang leader and a less than stellar mentor to Jax.

Check out the new photos of  Tisdale and McHale on this season of Sons of Anarchy:

 

Series creator Kurt Sutter recently discussed the highly anticipated fifth season Sons of Anarchy at this year’s Comic-Con. The show has already been renewed for a sixth season, but Sutter also touched upon the hit series’ potential end after season 7.

“This is the season about Jax at the head of that table and what kind of leader he will become. My sense of where the show will end up includes Jax and perhaps Gemma [Katey Sagal] and Clay. I don’t think the show continues without Jax because I believe in his journey. This season I have to write to that endgame; the stakes get higher, the circumstances get more dire, the wreckage gets deeper – and as a result, things will change. I don’t know how it all will fall apart, but eventually it will. The show is the prince’s journey. There is no show without Jax.”

Since the casting of both Tisdale and McHale was first announced, many hardcore SOA fans questioned both the teen queen and the funny man’s ability to fit into a mature drama like Sons of Anarchy. However, this isn’t the first time that the casting choices made by Sutter have initially appearedrisky (Tom Arnold and David Hasselhoff) but eventually turned out to be television master strokes.

Sons of Anarchy season 5 premieres Tuesday, Sept. 11th @10pm on FX.

Source: TV Line & The  Hollywood Reporter