In Episode 11 of the Cyrus Tries to Enjoy Himself podcast, Apollo joins Cyrus to discuss and reflect on his life as he navigates his way throughout the music industry.

In Episode 10 of the Cyrus Tries to Enjoy Himself podcast, Cyrus recaps the month of August and explains why he took last week off from the podcast. He then proceeds to discuss his most recent (self-titled) release, the passing of Chadwick Boseman, the current climate of the country, and closes the episode by tackling a few fan questions, while going significantly in depth on one question in particular.

In Episode 9 of the Cyrus Tries to Enjoy Himself podcast, Cyrus goes into detail about his upbringing, and reflects on the person he has become and the career he has established for himself.

In Episode 8 of the Cyrus Tries to Enjoy Himself podcast, Cyrus begins by sharing his potential post-COVID travel destinations, which quickly develops into a discussion about cannibalism and expresses that if he had to eat somebody, hypothetically, it'd be the guy in the middle seat on an airplane. Then, he discusses a Cartel soccer match that resulted in 16 deaths and 5 injuries, United Airlines forgetting a blind woman on an airplane, elephants and their synonymity with Vincent van Gogh, and whether he intends to put in an official application to join the QAnon movement.

In Episode 7 of the Cyrus Tries to Enjoy Himself podcast, Cyrus begins by discussing the turbulent week he's had, as well as the unfortunate revelation that he needs to begin looking for a new home. Then, he proceeds to discuss the hilarity behind people being in cover bands, the prevalence and significance of apps such as Tinder, Bumble, and Hinge in modern dating culture, COVID-19's impact on the touring industry, the explosion in Beirut, and the importance of considering one's own mental health above the needs and expectations of others.

In Episode 6 of the Cyrus Tries to Enjoy Himself podcast, MxRCUS ALEXIS joins Cyrus to reflect on the We Should Just Enjoy Ourselves Tour, their pre-pubescent discovery of pornography and masturbation, the importance of the bidet, and MxRCUS becoming a dad. Cyrus' also shares his thoughts after becoming the first rapper to officially enter the candle business.

In Episode 5 of the Cyrus Tries to Enjoy Himself podcast, Cyrus begins with a Q and A, and then proceeds to discuss current events such as $312 million USD worth of cocaine being seized on a submarine, Fauci‘s commitment to people not catching anything, especially baseballs, a man blowing up his backyard in an attempt to exterminate and resolve his cockroach infestation, and the unfortunate revelation of otters being murderous, necrophilic aqua-weasels.

In Episode 4 of the Cyrus Tries to Enjoy Himself podcast, Cyrus begins with a Q and A, and then proceeds to discuss current events such as the Pentagon banning all confederate flags and how he believes this ban should be extended to every flag ever, the looming civil war between pangolins and anteaters, and why Nick Cannon should make like his name and physically enter a cannon.

In Episode 3 of the Cyrus Tries to Enjoy Himself podcast, Cyrus begins with a Q and A, and then proceeds to discuss current events such as the ongoing Johnny Depp vs Amber Heard libel trial, Kanye West running for president, and Donald Trump's commuting of Roger Stone's sentence, before finally annotating the recent We Should Just Enjoy Ourselves remaster.