The second season of the Theme Time Radio Hour began on September 19, 2007, and ended April 2, 2008.
As in Season 1, Ellen Barkin opened the show, announcing the "Hello" episode with the lines: "It's night time in the big city.
This was a comedy segment featuring a listener call, supposedly as Dylan broadcast the show live from "Studio B."
In early October 2007, ISIS magazine and UK-based oldies label Chrome Dreams announced its release of The Best of Bob Dylan's Theme Time Radio Hour, an unauthorized 2-CD compilation featuring selections - out of copyright in the EU - from the TTRH Season 1 playlist.
The UK label Ace Records, released its own TTRH 2-CD compilation, Theme Time Radio Hour with Your Host, Bob Dylan, in March 2008, publicizing its set as "authorized", and compiled by TTRH producer, Eddie Gorodetsky and Dylan factotum, Jeff Rosen.
In the summer of 2008, ISIS magazine released The Best of Bob Dylan's Theme Time Radio Hour: Volume 2.
The Ace set features a broader - and a better representative - mix of music from TTRH than either of the ISIS/Chrome Dreams compilations, including selections from The White Stripes and The Clash.
None of the sets include any commentary from Dylan or other material from Theme Time Radio Hour.
During the "Days of the Week" show broadcast in October 2007, Dylan received a supposed email from listener, "Jackie Vann" who wrote in part, "...what is your take on Sheryl Crow using Buddy Holly's great Not Fade Away for a TV hair dye commercial?
Dylan responded with a list of artists "proud of commercial affiliation", including Sonny Boy Williamson, Jimmie Rodgers, and himself.
Later in October 2007, the Cadillac luxury car and SUV division of General Motors and XM Radio released a cross-promotional advertising campaign featuring Bob Dylan and Theme Time Radio Hour.
As could be expected, Dylan's participation was greeted with almost universal criticism from both the mainstream press and Web commentators.
Each of the scenes illustrated in the poster refer to Ellen Barkin's "It's Night in the Big City," introductions from Season 1 of TTRH.
Fan Simon Nielsen (aka "ukulele.elvis") would later create a multimedia walkthrough of the TTRH poster, using Ellen Barkin's introductions as the voiceover.
The walkthrough was also featured on BoingBoing, and Nielsen received a congratulatory email from XM Chief Creative Officer, Lee Abrams, on his initiative.
A print version of the poster was offered to the first 5,000 people to order any one of the three Bootleg Series Volume 8: Tell Tale Signs packages being sold through the site.
Later that year TTRH would do a second "Countdown" show, with all-new material, the series first theme to cross two seasons.
During the "Lock & Key" show broadcast in January 2008, Dylan lectured a supposed telephone caller, "Tim Ziegler", arguing that Theme Time Radio Hour "isn't a classroom," after Ziegler complained that Dylan had gotten a record label wrong.
In March 2008, Lee Abrams, XM Radio Chief Creative Officer and the person who brought Dylan to the station, announced that he was moving to a new job at the Tribune Company beginning April 1, 2008.
Also that month, the U.S. Department of Justice announced that it had approved the buyout of XM Radio by Sirius Satellite Radio, removing one major roadblock to the proposed merger which was eventually completed in late July 2008.
There was some fan speculation in online forums that Season Two came to an unplanned, early close possibly caused by Abrams departure, the Sirius merger, or some other, unknown reason.