By 2008, Dunham's characters had crossed language barriers, with his specials dubbed for audiences in various countries such as France, and Dunham attracting requests for performances in South Africa, Australia, Norway, Denmark, China, and the Middle East. Jeff Dunham's Very Special Christmas Special was taped at the Pabst Theater in Milwaukee, Wisconsin that same year, and premiered on Comedy Central on November 16, 2008, watched by 6.6 million people. It became available on DVD and Blu-ray on November 18, 2008. The special's premiere was the highest rated telecast in Comedy Central's history.
In September 2008, his career reached new heights as he began performing in arenas filled with tens of thousands of people. Dunham was somewhat wary of such large venues, but adapted by adjusting the timing of his often rapid exchanges with the puppets so that audience members farthest from the stage could have time to react.
In addition to his comedy specials, Dunham also released his first music album, Don't Come Home for Christmas, on November 4, 2008. It contains original Christmas songs as well as a parody of "Jingle Bells" by Achmed entitled "Jingle Bombs". All the songs, with the exception of "Jingle Bombs", were written and accompanied by Brian Haner, who joined Dunham's act as "Guitar Guy". His first onscreen appearance was in Jeff Dunham's Very Special Christmas Special.
In January 2008, Dunham was voted by fans the Top Comic in Comedy Central's "Stand-Up Showdown". He is the only person ever to win the "Ventriloquist of the Year" Award twice, was nominated "Comedian of the Year" by the TNN Music City News Country Awards, and has drawn praise from the Dallas Morning News for his technique and timing. Critics, such as Randee Dawn of The Hollywood Reporter, accused Dunham's characters of being racist caricatures, sexist, and homophobic.
In 2008, a TV commercial for a ringtone which featured Dunham's character Achmed the Dead Terrorist (see Characters below) was banned by the South African Advertising Standards Authority after a complaint was filed by a citizen stating that the ad was offensive to Muslims, and portrayed all Muslims as terrorists. Dunham responded that "Achmed makes it clear in my act that he is not Muslim." However, the ASA noted that the name Achmed was of Arab origin and was one of the names of Muhammad. Dunham responded, "I've skewered whites, blacks, Hispanics, Christians, Jews, Muslims, gays, straights, rednecks, addicts, the elderly, and my wife. As a standup comic, it is my job to make the majority of people laugh, and I believe that comedy is the last true form of free speech ... I'm considering renaming Achmed 'Bill'", he added. Dunham has conceded that he does exhibit particular sensitivity to the "conservative country crowd," or those characterized by "basic Christian values", as they are one of his largest constituencies, and part of his upbringing.