In their time at SNL, The Lonely Island pioneered the digital short format, creating popular sketches such as "Lazy Sunday", "I Just Had Sex", "I'm on a Boat", and "Dick in a Box".

[4] Theater director Tony Taccone brought home the film Cat on a Hot Tin Roof, a choice the other men teased as being "too theatrical".

[4] On the Internet, Schaffer got his start directing The Lonely Island's The 'Bu, the group's record-breaking contribution to Channel 101, which was a parody of The OC and starred Sarah Chalke as Melissa, as well as Samberg and Taccone.

[4] Some notable shorts/songs include "Lazy Sunday", "I Just Had Sex", "Natalie's Rap", "Dick in a Box", "Peyton Manning for the United Way", "Iran So Far", "Jizz in My Pants", "Boombox", "I'm on a Boat", "Great Day", "Threw It on the Ground", "Jack Sparrow", "Like A Boss", "YOLO", "Semicolon", "Dear Sister", "Spring Break Anthem", "Shy Ronnie", "Ras Trent" and "Motherlover", the sequel to "Dick in a Box".

In 2007, Schaffer directed and acted in the film Hot Rod, which starred Samberg, Taccone, Bill Hader, Danny McBride, Isla Fisher, Ian McShane, and Sissy Spacek, which was produced by SNL's Lorne Michaels.

[6][better source needed] Schaffer directed the film The Watch starring Ben Stiller, Vince Vaughn, Jonah Hill and Richard Ayoade, and written by Seth Rogen and Evan Goldberg.

[7] The film focuses on pop/rap superstar Conner4Real (Samberg), who goes into a major tailspin and watches his celebrity high life collapse after his new album fails to sell records.

[7] Also in 2019, they released Netflix's The Unauthorized Bash Brothers Experience, a visual poem about former Oakland A's legends Jose Canseco and Mark McGwire.

[7] That summer, The Lonely Island embarked on their first ever live tour, instantly selling out venues across the United States and drawing some of the biggest crowds of the weekend at the Bonnaroo Festival and Milwaukee's Summerfest.

[12][better source needed] Schaffer also executive produces Hulu's Emmy nominated show, PEN15, starring Maya Erskine and Anna Konkle.