The Worst Kind of Thoughtful is the first comedy special of its kind. Based on the 2018 comedy album by Mike Vecchione, it stars actors, artists, friends, fans, and many of your favorite comedians. It's the first User Generated Comedy Special.
After the sudden death of her parents, Maria faces foreclosure of the family home, a brain-injured brother, and a strange hum that only she hears.
Aging local standup comic Sweeney, "The Character King", gets an opportunity to do a national cable show out of Los Angeles. The only caveat is that Sweeney must drop the locally referenced material from his act, the biggest pieces being the portrayal of his colorful Boston "characters," that have become a staple of his home field success. Sweeney makes the hard decision to stop doing the characters. But, to his dismay, the characters "come-to-life" and seek their revenge; they try to kill Sweeney.
Uptight and straight-laced, FBI Special Agent Sarah Ashburn is a methodical investigator with a reputation for excellence--and hyper-arrogance. Shannon Mullins, one of Boston P.D.'s "finest," is foul-mouthed and has a very short fuse, and uses her gut instinct and street smarts to catch the most elusive criminals. Neither has ever had a partner, or a friend for that matter. When these two wildly incompatible law officers join forces to bring down a ruthless drug lord, they become the last thing anyone expected: buddies.
Doug MacRay is a longtime thief, who, smarter than the rest of his crew, is looking for his chance to exit the game. When a bank job leads to the group kidnapping an attractive branch manager, he takes on the role of monitoring her – but their burgeoning relationship threatens to unveil the identities of Doug and his crew to the FBI Agent who is on their case.
Lovestruck Dustin is dating Alexis, his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his best friend Tank to take her on the worst rebound date imaginable - his side job - so that she will come running back to him, and Tank reluctantly agrees. However, Alexis is more than a match for Tank's shock tactics and he begins to really fall for her, leaving him torn between loyalty to Dustin and his growing attraction toward Alexis.
After building his dream house, architect Newton Davis proposes marriage to his girlfriend, only to be summarily rejected. He seeks solace in a one-night stand with a waitress, never imagining that a woman he slept with once would end up posing as his wife. Gwen's ruse is so effective that by the time Newton learns of his "marriage," the entire town feels like they know him.
Shakes plods about his duties as party clown, and uses all of his free time getting seriously drunk. Binky, another clown, wins the spot on a local kiddie show, which depresses Shakes even more, and his boss threatens him with unemployment if he can't get his act under control.