Alan Pentland

Often people with creative desires are unsure if a career in the arts is a realistic ambition. This is exactly what Alan Pentland (Class of 1970) used to wonder: “How could an ordinary person like me ever claim to be an artist?”


‘Science geek’

Alan Pentland who describes himself as a ‘science geek’ during his time at Caulfield Grammar School, enjoyed studying Latin, French and Esperanto. It was as a result of this interest in language and words that his passion for poetry and comedy began to grow. During Years 11 and 12, Alan along with Steven Lee (another past student) published a poetry newsletter called No Dominion, and in 1970 Alan won the CGS Poetry Award.


This creative encouragement was one of the things Alan loved most about his time at Caulfield. It was a great environment to prosper intellectually, as it celebrated liberal thinking and being open minded. He saw that if a student had a vision for a project, they were supported by the school. The one thing Alan couldn’t do was wood working – unfortunately there were no facilities for it! Alan also enjoyed his trips to Yarra Junction where students participated in literary camps, personal development and building traps to catch rabbits and yabbies. It was also a great way to connect with boarders from rural backgrounds on their terms.


After high school Alan went on to qualify as an architect at Melbourne University, however, he only practiced as an architect for three days! What he noticed from this short foray was that a lot of potential architects ended up as comedians. This was the impetus Alan needed to pursue his passion for comedy, proving it doesn’t matter what you study, it’s the people you meet!


A career in comedy

Alan Pentland went on to run Melbourne’s first stand up club, Le Joke, work with Daryl Somers (Hey Hey It’s Saturday) and was a key player in the TV comedy Fast Forward, winning two Logies and two Writers Guild awards. His work on Darwin’s Human Race, a two-minute summary of the theory of evolution that he wrote and performed, won Best Animation at Sydney Film Festival, Colorado Mountain Festival (1999) and Nashville Film Festival (2000). Alan was also the Script Executive on the two seasons of Jimeoin. After 25 years of working in television, he then moved on to marketing communications, where he was recognised by the CEO of Telstra for outstanding achievements. Alan also worked as a communications consultant for Talk Sense, for which he wrote “Talk Sense – A practical guide for good communicators”.


In 2016, Alan returned to writing and performing poetry. In 2017 he won a Slam poetry competition and the Melbourne Spoken Word Prize, coming full circle from his 1970 Caulfield Poetry Award. He now regularly performs spoken word to diverse audiences, describing his style as ‘intelligent entertainment’.


Holiday host

Alan is now semi-retired and lives on French Island with his wife Mylene. Together they run a low-key holiday retreat – French Island Cottage. Managing the retreat involves a lot of physical work as it sits on 75-acres which Alan is restoring to bushland. Alan still makes space for comedy in his retirement and can often be found crafting a new joke.


Irrespective of whether Alan is performing poetry or hosting guests at his cottage, the best thing is still meeting new people and having interesting conversations. Reflecting back on his career, Alan believes that one should trust their instincts, even when it’s scary. In the future Alan hopes to continue trying new things and dealing with the world by laughing at it.


Read more profiles on our Caulfield Grammar School alumni working in the entertainment industry including Ellen Shanley (Writing for Television) and Dylan Lewis (Radio Personality).


Want to connect with Alan? You can find him on:



Feature image courtesy of Alan Pentland.

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