Performing as a duo with another young man, they presented Smutty and Pert, like Ernie and Bert (from Sesame Street.

[6] In the same year, he developed and performed his show Death of a Sails-Man, which one reviewer described as "an extremely quirky one-man monologue... a man live on stage having a breakdown, singing, reflecting and joking with his sub-conscious".

[7] His 2015 award-winning show, Spaghetti for Breakfast featured his usual "silly" (self-described) pieces, followed by a deeply personal reference to how he nearly committed suicide as a young adolescent.

[4] When in Los Angeles, he did regular shows with Dr Brown (Phil Burgers), and they worked together on developing a TV series.

[4] After living for some time across three cities (Sydney, Los Angeles, and London, he announced early in 2019 that he was going to quit touring with live comedy for a while after his current commitments with his new show, 26 Things You're Doing Wrong with Sam Simmons, although still intending to do some acting and write TV scripts.

[10] In December 2019, he performed for 10 nights at the Soho Theatre in London,[11][12] and in 2020 was working on a solo show called FUNT there.

[1] In March 2024, Simmons performed his new show Man With A Fork In A World Full Of Soup at the Adelaide Fringe, which earned good reviews.

[5] He was a regular guest host and contributor on JTV from 2007 to 2009 This led to his first television show, The Urban Monkey with Murray Foote, in 2009.

After moving from Adelaide to Los Angeles, in 2013 he filmed a US pilot in Albuquerque with David Quirk, described by Simmons as "a reality show about animals".

[4] In February 2019, Simmons revealed that he was father to a baby, and wanted to spend some time enjoying family life.