Dear Santa has such a fun concept behind it, a kid with dyslexia accidentally misspells Santa for Satan and it is mailed to Hell. Although, if we are looking at this with logic, the name shouldn’t matter with the North Pole address being correct. Nonetheless it lands in the eternal fire pit with “you know who” there to retrieve the parcel. 

 

Jack Black is that man, the big cheese of Hell, AKA Satan. Intrigued by a letter requesting gifts from a young kid, he travels to the mortal realm to introduce himself. Shortly after he figures out the young Liam Turner (Robert Timothy Smith) has a learning disability, he decides to continue on his path to granting three wishes for the kid under the disguise of Saint Nick. 

 

From a desire to have a girl look his way to hanging backstage with Post Malone, Liam is living his best life but being careful while he does it after realizing that his friend Santa is actually The Devil. Naturally when you play games with Lucifier things get out of hand and Liam risks his soul if he were to cast a final wish.

 

The biggest fact to look into when it comes to Dear Santa is just how much entertainment do you get out of Jack Black’s presence alone? If you get nothing from a Jack Black performance then this film is a bonafide flop for you. Even as a massive fan of Black, I was struggling to find much entertainment. 

 

Young Robert Timothy Smith is perfectly fine in the role, his cluelessness and childish charm makes his performance all the more fun to watch surrounding this crazy mixture of tone. The same goes for a bunch of the other child actors as they are not necessarily the best of actors, but their connection and friendships feel almost natural because of their age. However, a few of the storylines the script decides to utilize for their friendship involving a faking of cancer and the real death of a sibling leaves almost a bitter taste in an otherwise silly experience. 

 

Keegan Michael-Key has a swift entrance and exit from the film, delivering some decent chuckles as a child psychologist listening to Liam’s “tall tales” about the devil being his friend. Liam’s parents having talk of divorce and nervousness around their son’s recent behavior skyrockets to irrational levels as they go to the extreme to lock him into a mental institution at one point. This is a fine-point example of how crazy this story goes for absolutely no reason.

 

A particular cameo reveals a massive plot twist that completely alters the story at the last minute. Dear Santa is a confusing holiday film from the filmmakers that brought us such classics as Dumb and Dumber and There’s Something About Mary. It misses the mark more than it manages to nail and its decision to not have a consistent tone leads to an exhausting experience in the end. Jack Black fans may have a laugh or two, but his presence alone can’t save Dear Santa.