Season 2 of The Naked Brothers Band follows the band in another set of misadventures as well as the band's first national tour. The first half of the season kicks off with a preformance at the middle school dance (Sidekicks), and the band shortly deals with many situations such as a water park vacation (Great Trip), movie dates (Three Is Enough), interviews (Talk Show), Jewish traditions (The Bar Mitzvah), and sibling superiority (Uncle Miles), as well as last-minute issues before they leave to go on tour (Everybody's Cried At Least Once). Away from home, the band gets all kinds of attention as the cellist of the band gets love from a certain city (Cleveland), while the whole band disguises themselves from crowds while interacting with local folks (The County Fair). The season concludes with a hour-long emotional finale about global awareness, negative publicity from press, and a very confusing love triangle (Polar Bears).
A TV special of the titled County Fair Concert Special was broadcast on May 24, 2008, and shows the band preforming various songs from the past two seasons (including the movie) at the Rye Playland in Rye, New York.
All of the fourteen songs featured in this season (including the single I Don't Want To Go To School) was released in a official sountrack titled after the aforementioned single on April 15, 2008 under the Nickelodeon/Columbia label.
A DVD of all the episodes from this season was released on October 21, 2008 by Nickelodeon and Paramount Home Entertainment, and included special features such as music videos, short clips, and behind the scene extras.
| 1||Sidekicks|| January 21, 2008|
|2|| Great Trip|| February 2, 2008|
|3|| Three Is Enough|| February 9, 2008|
|4|| The Talk Show|| February 16, 2008|
|5|| The Bar Mitzvah||February 23, 2008|
|6|| Uncle Miles|| March 8, 2008|
|7|| Everybody's Cried At Least Once|| April 12, 2008|
|8|| Cleveland|| April 19, 2008|
|9|| The County Fair|| May 10, 2008|
| 10|| Polar Bears|| June 8, 2008|