Comedy films get slept on by audiences way too often.
It doesn’t help that theatrical releases for comedy films are nowhere near their heyday, but that doesn’t mean there aren’t funny films, both new and old, that still deserve your attention.
This month, Watch With Us is highlighting three underrated comedies that you can watch on Amazon, Tubi, and The Roku Channel, including a Lonely Island-led mockumentary, a Seth Rogen black comedy, and Matthew McConaughey as the funniest pothead ever.
Read on to see the top picks for October 2025.
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‘Observe and Report’ (2009)
Mall cop Ronnie Barnhardt (Rogen) takes his job extremely seriously, even when nobody else does. In reality, Ronnie is deeply incompetent but believes he has what it takes to be a real policeman. When he’s confronted by Detective Harrison (Ray Liotta) after a flasher terrorizes his mall, he takes the opportunity to prove himself to be a man of the law. He tries to bring the pervert to justice while simultaneously applying to the police academy and trying to impress his crush, beauty counter worker Brandi (Anna Faris).
Observe and Report may have confused audiences at the time, expecting another Superbad or Knocked Up, and instead got an incredibly bleak, black comedy about a mentally ill mall cop with delusions of grandeur who takes it upon himself to act as a vigilante. The film is ultimately an indictment of white male disenfranchisement, entitlement, masculinity, and the dangers of male insecurity complexes; a Seth Rogen-ified hybrid of Taxi Driver and Joker. It’s as smart as it is upsetting, and will make you squirm in your seat as much as it makes you laugh uncomfortably.
Watch Observe and Report now on The Roku Channel.
‘Pop Star: Never Stop Never Stopping’ (2016)
Pop icon Conner Friel AKA Conner4Real (Andy Samberg) broke away from his music group “The Style Boyz” with his childhood friends, and went on to become a successful solo musician with his first record, “Thriller, Also.” However, surrounded by “yes men” and with a skyrocketing ego, Conner’s sophomore album proves to be anything but perfect. This mockumentary chronicles Conner4Real’s rise to solo stardom and fall from grace, as he struggles to pick up the pieces and regain the goodwill of his fans.
From the Lonely Island comedy troupe of Samberg, Jorma Taccone and Akiva Schaffer, Pop Star: Never Stop Never Stopping flopped at the box office upon release but has gone on to cultivate a passionate cult following. It’s frequently regarded as one of the best comedies of the 2010s and a scathing parody of the pop star documentary industrial complex. It balances absurd humor with laugh-out-loud vulgarity and sharp satire, and the fake songs are better than some real ones.
Rent Pop Star: Never Stop Never Stopping on Amazon Prime Video.
‘The Beach Bum’ (2019)
Writer Moondog (McConaughey) is an acclaimed poet who also just happens to be a hedonistic stoner who doesn’t live by any rules other than “have a good time, all the time.” He leads his devil-may-care life, getting as drunk and as high as possible, the results of which tend to vary when it comes to finishing his new novel. However, a tragic accident turns Moondog’s world upside down, bringing tensions with his daughter, Heather (Stefania LaVie Owen), into sharp relief. Can Moondog keep partying, or is it finally time to slow down?
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The Beach Bum is a work of manic comedic bliss and features an absolutely career-best goofball performance from Matthew McConaughey. While some viewers may not vibe with an aimless, laid-back narrative, those who are willing to chill out and just go on a ride with Moondog are in for a film of sumptuous delights. As indulgent and decadent as its protagonist, The Beach Bum is a funny, affecting ode to doing what makes you happy and finding what matters most to you.
Watch The Beach Bum now on Tubi.
