The first three videos, all of which were shot in Los Angeles and are under 10 minutes long, debuted on Wednesday on the popular site where users can find a job or an apartment or sell the contents of their garage.
In one segment, a bubbly 28-year-old named Charity posts an "Open Casting Call" for a husband. The camera follows her one-on-one meetings with a host of bachelors -- one who brings a pineapple as a gift -- and telling her father about her latest adventure.
"He's not approving, but that's how daddies are -- they're not approving," she tells the camera.
In another segment, a budding fashion designer posts an ad on Craigslist to movie star Sandra Bullock, saying he wants to design her Oscar dress. As the days count down to the big night and Bullock does not respond, the increasingly nervous designer hires look-alikes to model the gown instead.
In March, Craigslist allowed users to check an "opt in" box next to their online ads that indicated they would like to have their adventures chronicled online.
The videos, produced by Brownstone Entertainment, are posted on YouTube and on Craigslist.
Craigslist, a privately owned company based in San Francisco, is the largest US classifieds site, with more than 50 million US users. It also operates globally.
In addition to ads for cars and jobs, the site offers personal ads, which include missed connections and casual encounters.
The company has faced pressure in the past year over paid-sex ads found on its site. But Craigslist says it quickly takes down offending postings and has done more than competitors to battle human trafficking and exploitation.