- Wickenden performed with Scottsdale's Oxymoron'Z improv troupe from 1995-96.
- At the 2016 Cinema Eye Honors, Wickenden and Albert Maysles were the only two filmmakers to be nominated for their work on two separate films. For Maysles it was "Iris" and "In Transit" and for Wickenden it was for "Best of Enemies" and "Almost There".
- In 2014 Wickenden was chosen as one of the top 10 filmmakers working in Chicago by New City who went on to call him "an unassuming but essential talent... [with] a knack for structure and for rhythms". He was again honored by New City in 2016 who chose him as one of the top 5 filmmakers working from Chicago, and then again in 2018 when New City ranked him as the number two filmmaker working in Chicago, after Wickenden's mentor Steve James.
- Wickenden was mentored by acclaimed director Steve James for nearly a decade (2002 - 2011). This relationship began via an internship at Chicago's Kartemquin Films, progressed as Wickenden assisted on "Reel Paradise", post supervised "The War Tapes" and would culminate in Wickenden editing two films with James.
- As of 2022, he has contributed with the editing of three films that were nominated for the Independent Spirit Award for Best Documentary Feature: "The Interrupters" (2011), "Best of Enemies" (2015) and "Won't You be My Neighbor?" (2019). Of those, "The Interrupters" and "Won't You be My Neighbor?" were winners in the category.
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