Caspar Pennington is the primary antagonist of the 2005 Canadian family comedy film, Bailey's Billion$. He is a lawyer, Dolores Pennington's husband, and the late Constance Pennington's greedy nephew who runs a secret illegal puppy mill called Waggly Tail Puppies.

He was portrayed by Tim Curry who also played Frank-N-Furter in The Rocky Horror Picture Show, Lord of Darkness in Legend, Wadsworth in Clue, Pennywise in the It television miniseries, Thaddeus E. Klang in TaleSpin, Taurus Bulba in Darkwing Duck, Hexxus in FernGully: The Last Rainforest, Evil Manta in The Little Mermaid television series, Farley Claymore in The Shadow, Kilokahn in Super Human Samurai Syber-Squad, Drake in The Pebble and the Penguin, Dr. Anton Sevarius in Gargoyles, Long John Silver in Muppets Treasure Island, Lord Dragaunus in the Mighty Ducks TV series, Simon Doonan in the Titanic TV movie, Maestro Forte in Beauty and the Beast: The Enchanted Christmas, Kilokahn in Super Human Samurai Syber Squad, Slagar the Cruel in Redwall, Dr. Slicer in Recess, Ben Ravencroft in Scooby-Doo and the Witch's Ghost, Goblin King in Scooby-Doo and the Goblin King, Pretorius in the TV series The Mask, Rooster St. Regis in Annie, Professor Oldman in Scary Movie 2, Big Brother in Johnny Bravo, Mouse King in Barbie in the Nutcracker, Professor Calamitous in The Adventures of Jimmy Neutron: Boy Genius, Scarlet Fever and Nick O' Teen in Ozzy & Drix, Skullmaster in Mighty Max, Dale "The Whale" Biederbeck in Monk, Belial in The Legend of Atlantis, El Maléfico in ¡Mucha Luca!: The Return of El Maléfico, Cardinal Richelieu in The Three Musketeers, Von Talon in Valiant, Kileem, Amok Mon Ra, and Caliph Kapok in the Aladdin TV series, Fox Jacket in Dinosaurs, one of the Sub-humans in Fire and Ice, Worthington Dubois and Lloyd Wexler in Phineas and Ferb, Anatoly Cherdenko in Command and Conquer: Red Alert 3, Trymon in Terry Pratchett's The Color of Magic, The Cat King in The Cat Returns, Philippe in Barbie and The Three Musketeers, Farley Claymore in The Shadow, King Chicken in Duckman, Billy Flynn in Criminal Minds, Konk in The Pirates of Dark Water, and Emperor Palpatine in Star Wars: The Clone Wars.

Personality[]

Like his wife, Dolores, Caspar Pennington is shown to be mean, cruel, selfish, greedy, lying, vain, temperamental, careless, money and power-hungry, impatient, sadistic, abusive, threatening, and sarcastic. He has a deep affinity of animals; especially, dogs even more than he hates opera music as seen when reprimanding one of his puppy mill workers for listening to opera music while on the job.

Despite the love for his wife, he can only put up with her constant whining and nagging for so long up to a point where he eventually either mocks or insults her. Though apparently angry about not inheriting his late aunt's fortune as he had hoped at first, Caspar appears more clever and rational when he plots to kidnap and ransom Bailey rather than kill him first as suggested by his wife in order to avoid suspicions and later, to discredit Ted Maxwell as an irresponsible, incompetent guardian of Bailey in order to gain custody of both the dog and eventually, the fortune, of course.

However, when it seems that both he and his wife have lost once their crimes have been exposed in court, Caspar will go to great lengths to try just about anything to avoid arrest even if it means betraying his own wife by putting all the blame on her for everything, but to no avail.

Biography[]

In Toronto, a week after the recent death of his elderly but wealthy and philanthropic Aunt Constance, Caspar Pennington drives his never-ending whining and nagging wife, Dolores in a limo to his late aunt's estate for the reading of the latter's will. Being her only dearly beloved nephew, Caspar believes that he and his wife will inherit his late aunt's fortune once they arrive at the mansion. After getting sprinkled with water and his wife accidentally steps on his foot as she gets out of the limo, Caspar and Dolores make their way to the estate. Once inside, Caspar watches with shock as his late aunt's favorite 7 year old dog, Bailey the Golden Retriever attacks his wife's tippet before they enter the music room with Bailey's translator/canine behaviorist, Theodore "Ted" Maxwell to proceed with the reading of the will.

In the music room, Caspar and everyone else sit down to listen and watch his late aunt's will on a recording on-screen. Once Caspar and Dolores's turn comes up, they are shocked to discover that, although Caspar was always considered like a son to her, both are charged with running the day-to-day operations at ARRF (Animal Rights and Research Foundation which she ran and that cared for and found homes for stray dogs everywhere) since she feared that everything her nephew ever wanted and got didn't serve him well whereas Bailey is appointed ARRF's new CEO boss and inherits both her estate, house, jewelry, money, and all of her investments and Ted is entrusted with guardianship of Bailey (Miles "Mouse" and Peggy Delaney, the servants are given $50,000 each and 1% of her stocks in bonds). Angered and frustrated, Caspar and Dolores leave the room despite Bailey trying to make up with them as suggested by Ted.

At their home, Caspar reads the paper while reluctantly listening to his wife constantly whine, nag, and later, throw a tantrum about their current situation other than the fact that they're almost broke and in debt. Later, Caspar and Dolores enter a secret illegal puppy mill (which the former prefers to call a "money mill" instead) they secretly run within ARRF behind everyone's back called Waggly Tail Puppies as they boast about how they'll make millions of dollars once they return their profits.

A few days later, Caspar begins mocking his wife's never-ending whining and nagging before they enter their first board meeting with Bailey as the newly-appointed CEO boss and Ted serving as his translator. During the meeting, when an employee named Harry Innis points out that the foundation's trust account appears to be empty, Caspar and Dolores try to brush it off as being "moved to an offshore account for tax reasons beyond comprehension" even though Bailey "thinks" that they should've cleared the decision to move the trust offshore with the board since funds can't be moved without the board's approval; hiding the fact that they've actually embezzled it to finance their secret illegal puppy mill operation. Later, Caspar spoils a somewhat romantic moment between Ted and the receptionist, Mrs. Margery "Marge" Maggs as he points out to the latter that the phones are ringing.

At night, at their home, being a lawyer, Caspar listens to his wife whine and nag once again as he tries to find an angle within their situation. When Dolores suggests that they simply kill Bailey, Caspar cleverly points out that they will both be the first suspects when it comes to "doggy murder most foul" before his wife throws her skirt at him in anger and frustration. That's when Caspar finally comes up the idea of kidnapping and holding Bailey for ransom instead, which suddenly delights the greedy couple before they accidentally fall into their own pool and laugh evilly with joy while dancing and hopping with joy at their most fiendish plan yet.

The next day, Caspar and Dolores watch Bailey from their car and wait until Ted leaves his side in the car before they can make their move as they laugh wickedly. Unfortunately, their plan fails when they see both Bailey and Ted leaving together; much to their chagrin. Then, they watch Ted and Bailey with Marge, her daughter, Samantha, and their dog, Tessa as Dolores naively points out that if both Bailey and Tessa have puppies, they will be next in line for the inheritance.

The following day, after Caspar carelessly fires Harry and reminds Marge of the rule about bringing both her daughter and the latter's new friend, Max Rizzo to work, he makes his way to his puppy mill; unaware that he's being followed by Tessa and the kids who eventually discover the operation even before Max takes a picture of it afterwards. At the mill, Caspar laments at his temporary failure. Then, Caspar tells one of his workers to turn off the opera music playing within the place and reprimands him before leaving again.

The next morning, Caspar sarcastically thanks Marge for taking over for Harry while maliciously promising no extra in her paycheck though. At night, Caspar and Dolores begin to execute their plan by sneaking inside the mansion and trying to kidnap Bailey while dressed in black, only to find themselves foiled by the unexpected intervention of Mouse and Peggy; unaware that Bailey and Ted already left to investigate the puppy mill's possible existence. After escaping despite sustaining certain injuries, Caspar and Dolores begin to argue somewhere in the bushes. When Bailey and Ted finally return home, Caspar and Dolores finally manage to kidnap Bailey when they notice him heading their way alone.

In the morning, while they recover from their injuries, Caspar comes up with a better idea than ransoming Bailey as he states that with the dog "lost", he can discredit Ted as an incompetent, irresponsible guardian. Then, Caspar and his wife find themselves confronted by Marge about the foundation's records then by Samantha when she points out that she, Max, and Ted saw their operation in action at night. Nevertheless, Caspar and his wife simply brush off all suspicions as they try to convince them that Ted is a madman and con artist before revealing that they intend to take the will to the court of appeal and carelessly firing Marge as well on a matter of "downsizing".

Later, at home, Caspar is enjoying some time playing at the pool with his toy boat until he receives an unexpected visit from Don Donald the social worker of the HCS (Home Children Services) who has been hounding Marge for years for her animal activism. News of Marge and her past involvement in animal activism naturally intrigues and delights Caspar and his wife, knowing they can use this to their advantage against her by providing Donald with extra false information about her.

Back at the puppy mill, Caspar and his wife visit, taunt, and mock Bailey currently held in a cage there. Then, when Caspar wonders why they can't kill Bailey now, he listens to his wife's latest plan about making it look like they had found him after the latter had gone "missing" and passing themselves off as "heroes", thus, allowing them to petition the court for guardianship of Bailey as his "true, rightful owners" and control both him and the entire fortune before dancing and hopping with joy at their latest fiendish plan yet.

Then, Caspar and Dolores are in a press conference falsely imploring Bailey's "safe return" home. At night, Caspar and his wife celebrate their supposed success with another dance-hop until Marge barges in, asking about her daughter and the latter's friend's whereabouts as she suspects they might've snuck into ARRF. After Caspar and his wife reassure Marge otherwise, they don't hesitate to escort the latter out of the building. However, Caspar and his wife eventually discover the kids have indeed snuck in with Tessa in order to save Bailey, but have found themselves trapped otherwise either way. When Caspar suddenly finds himself attacked by Marge from behind, one of his workers restrains her before his wife chloroforms her. Then, Caspar orders his worker to keep the kids in here, make sure they don't escape, and chloroform Bailey.

The next day, at court, Caspar executes his plan to ensure he and his wife get exactly what they want in the end. With Ted unavailable due to having gone to rescue his friends, Caspar has his wife bring in Bailey to court as planned like as though the latter had found her after making his way back to the foundation. However, just when it looks like they've finally won, Ted, Marge, the kids, and Tessa come in just in time to expose the Penningtons of their crimes against animal welfare with photographic evidence despite their vain protests. Completely defenseless, Caspar tries in vain to put all the blame on his wife for everything before they are both taken away by bailiffs and guards and eventually arrested for their crimes.

With the Penningtons arrested, Ted still retains full legal guardianship of Bailey and Marge is rehired, promoted, and given a raise by Bailey, thus, making Donald lose any chance of taking Samantha away again this time unlike 2 years ago. 6 months later, everyone opens a new place for stray dogs named Puppy Love Kennels.