He told The Daily Beast: "The very first video I did was for a band called The Shame Idols in Birmingham, Alabama, and I paid for it on a credit card and my mom loaned me about $500 to finish it.

"[7] Between 1999 and 2009, he directed videos for the likes of Good Charlotte, Evanescence, AFI, 3 Doors Down, Green Day, My Chemical Romance, and Snow Patrol.

[8] His feature-length debut, 500 Days of Summer, starring Joseph Gordon-Levitt and Zooey Deschanel, was released in July 2009 to a positive critical reception.

[12][citation needed] Webb is represented by DNA in Hollywood, California and Academy Productions Ltd in the United Kingdom.

In February 2019, he signed on to direct the live-action reimagined version of the 2016 Japanese anime film Your Name [13] before he was replaced on September 18, 2020 by Lee Isaac Chung and a year later by Carlos López Estrada[14] In May 2019, it was announced that Webb will direct a live-action adaptation of Disney's Snow White and the Seven Dwarfs.

[15] In 2013, Christopher Keyser and Webb pitched the mystery drama The Society to Showtime, but the network later decided to pass on the series.

In Yellowcard's "Ocean Avenue" and "Rough Landing, Holly" videos, the lamb appears on a briefcase Ryan Key carries.