Stand-up Cross began performing
stand-up comedy around the age of 17. In 1990, a new comedy scene began to emerge at the comedy club chain
Catch a Rising Star. Alongside
Janeane Garofalo,
Louis C.K., and other comics, Cross appeared regularly several nights a week. Cross formed the sketch comedy group "Cross Comedy" with 12 other performers, and they put on a new show every week. They were known for playing tricks on the audience, such as introducing fake comics or planting fake
hecklers. Cross became increasingly focused on his comedy work. where Cross appears as OJ's valet. Cross also starred in the Joe Frank program "Jam", produced in 1999, and worked with Frank on radio shows for
KCRW's
Unfictional: "A Conversation" (2013) and "Downfall" (2015). Cross's stand-up comedy blends political commentary and satire. In 1999, he performed a one-hour comedy special,
The Pride Is Back, on
HBO. In 2003, he released his first tour film,
Let America Laugh, and was named No. 85 on Comedy Central's list of the 100 greatest stand-ups of all time. He has released five comedy albums: 2002's
Shut Up You Fucking Baby!, 2004's ''
It's Not Funny'', 2010's
Bigger and Blackerer, 2016's
Making America Great Again/
...America... Great..., and 2019's
Oh, Come On. He was nominated for the
Grammy Award for Best Comedy Album twice, in 2003 for
Shut Up You Fucking Baby! and in 2016 for
...America... Great.... Cross's first three records were released on CD by indie-rock label
Sub Pop, and on vinyl by comedy label
Stand Up! Records for
Shut Up and ''It's Not Funny''. He self-released 2016's
...America... Great... on CD, with Stand Up! again releasing a vinyl version.
Oh, Come On was released by Comedy Dynamics. Cross tends to release his albums in overlapping audio and video formats which each contain material not found on the other. This is the case on
Bigger and Blackerer,
Oh, Come On, and perhaps most obviously the 2016 companion set
Making America Great Again (a Netflix film) and
...America... Great... (CD/vinyl audio), which have different titles.
Oh, Come Ons video and audio versions were recorded at two different shows on the same tour. Cross's stand-up material was featured in
Comedy Central's 2004 animated series ''
Shorties Watchin' Shorties. He appears on several Un-Cabaret compilation albums, including Freak Weather Feels Different
and The Good, the Bad and the Drugly''.
Television, film and voice roles Cross began his professional television career as a writer on
The Ben Stiller Show. The series hired him toward the end of its run, and he occasionally made brief appearances in the sketches. He had a speaking role in "The Legend of T.J. O'Pootertoot", a sketch written almost entirely by Cross. It was during this period that he first met
Bob Odenkirk, with whom he would later co-create the HBO
sketch comedy series
Mr. Show with Bob and David (Mr. Show) in 1995. Cross won an Emmy for his work on
The Ben Stiller Show in 1993. In 1997 he played Newton, an employee of the NYC Morgue in
Men in Black, and reprised the character, now as an owner of a video rental store, in
Men in Black II in 2002. Cross later co-starred as
Tobias Fünke in
Arrested Development, originally intended to be only a minor role. He also played smaller roles on programs such as
Just Shoot Me!,
The Drew Carey Show,
NewsRadio,
Strangers with Candy,
Tim and Eric Awesome Show, Great Job, and
Aqua Teen Hunger Force. From October 2005, Cross regularly appeared on Comedy Central's
The Colbert Report as
Stephen Colbert's nemesis Russ Lieber, a fictional liberal radio talk show host from
Madison,
Wisconsin. Cross developed an animated series for Comedy Central called
Freak Show, which co-starred
H. Jon Benjamin and was cancelled due to low ratings. He has appeared several times on
Wonder Showzen. Cross teamed up with
Mr. Show director and producer
Troy Miller and Odenkirk to produce a feature film
Run Ronnie Run, based on one of their
Mr. Show characters. The film satirized the
reality television craze, and featured cameos from many stars; however, Odenkirk got into conflict with the studio
New Line Cinema, and they released it
direct-to-video. In 1994 and again in 1999, Cross was a guest voice actor on
Joe Frank's radio show, featured in the episodes "The Last Run", "A Hearing", "The O.J. Chronicles", and "Jam". In 2013, he returned, making an appearance in an episode of Frank's radio show, entitled "A Conversation". In 2004, Cross provided voices for a Marine in
Halo 2 and a store clerk named "Zero" in
Grand Theft Auto: San Andreas. He was also the voice of the "Happy-Time Harry" doll and Bert Banana in
Aqua Teen Hunger Force (although the part was credited as Sir Willups Brightslymoore). Cross has made guest appearances in
Tim and Eric Awesome Show, Great Job! He directed the music video for
The Black Keys' song "
10 A.M. Automatic", a spoof of
public-access television.
Paste Magazine ranked it number 24 on their list of the 50 Best Music Videos of the Decade (2000–2009). Cross appeared in
The Strokes' music video for "
Juicebox" as a bad local "morning zoo" radio DJ. He also appeared in
The New Pornographers' video for "Use It", in
Superchunk's video for "Watery Hands" (along with
Janeane Garofalo), and in
Yo La Tengo's video for "Sugarcube" (along with Bob Odenkirk and John Ennis). Cross contributes to
Vice magazine, writing a column,
My America. In 2005, he contributed to the
UNICEF benefit song "
Do They Know It's Hallowe'en?" and appeared in one of
PETA's "I'd Rather Go Naked Than Wear Fur" campaigns. In the
Beastie Boys' 2006 concert film ''
Awesome; I Fuckin' Shot That!, Cross portrays Nathaniel Hörnblowér in the fictional segment "A Day in the Life of Nathaniel Hörnblowér". In I'm Not There, Cross portrays Allen Ginsberg. Both Bill Lawrence and Zach Braff of the TV series Scrubs'' were eager to have Cross make a cameo appearance on the series as
Tobias Fünke, but due to the series' cancellation, the plan never came to fruition. Cross provided commentary on the
Vicarious music video
DVD for
Tool. He has previously performed comedy as an opening act for the band and its members appeared on
Mr. Show several times. He portrayed Ian Hawke in the
Alvin and the Chipmunks film series and voiced
Crane in the
Kung Fu Panda film franchise. Cross starred in ''David's Situation
, a pilot for HBO. It filmed in May 2008 and included many Mr. Show alumni at the taping. On August 6, 2008, Bob Odenkirk announced on bobanddavid.com that David's Situation'' would not be produced. Cross's
black comedy series
The Increasingly Poor Decisions of Todd Margaret, in which he stars and co-writes with
Shaun Pye, has run on
Channel 4 in the United Kingdom and
IFC in the United States since October 2010, for a total 18 episodes. On March 29, 2010, his first comedy special in six years,
Bigger and Blackerer, was streamed on
Epix HD. A CD with "slightly different content" was released on May 25, 2010. In 2009, Cross released his first book
I Drink for a Reason. The book features memoirs, satirical fictional memoirs, and material from Cross that originally appeared in other publications. In September 2009, Cross performed at his own comedy stage at the
ATP New York 2009 music festival, for which he picked
Eugene Mirman,
H. Jon Benjamin,
Jon Glaser, and
Derrick Brown & The Navy Gravy to join him. In the same year, Cross and Benjamin created and wrote for
Paid Programming on
Adult Swim.
Paid Programming was not picked up for a full series and Benjamin referred to it as an "abject failure". Cross starred alongside
Julia Stiles and
America Ferrera in ''
It's a Disaster'', which premiered at the 2012
Los Angeles Film Festival.
Oscilloscope Laboratories acquired US distribution rights to the film, releasing it in select theaters beginning April 13, 2013. Cross's directorial debut film
Hits premiered at the
2014 Sundance Film Festival. Instead of selling the film rights to distributors, Cross instead opted to sell the movie over
Bit Torrent through their "bundles" program, which BitTorrent launched to help "legitimize" the platform. It premiered in November 2015 on
Netflix. Cross and Odenkirk write, star in, and produce the show. On the January 10, 2016, broadcast of the National Public Radio-syndicated quiz show
Ask Me Another, Cross appeared as a celebrity guest and performed well enough that at the audience's request the show's producers took the unusual step of allowing him to advance to the show's final, championship round; he then won that round and became that episode's overall champion, winning a prize package that included a pair of denim cutoff shorts that he himself had autographed. He created the eight-episode
black comedy series
Bliss, which was released by the
BritBox streaming service in 2018. It stars
Stephen Mangan as Andrew, a fraudulent
travel writer, who is struggling to maintain long-term relationships with two partners, Kim (
Heather Graham) and Denise (
Jo Hartley), who are not aware of one another. The same year Cross provided the lead character's "white voice" in the
science fiction comedy film Sorry to Bother You (2018). On October 16, 2025, Cross guest starred as Nolan Hurst, in the TV series
Elsbeth, episode titled Doll Day Afternoon on
CBS. ==Influences==