"Josie" was named after the dog of Elyse Rogers, vocalist for Dance Hall Crashers, and the girl in the song is fictional. The line "Yeah my girlfriend, likes UL and DHC" is a reference to the bands Unwritten Law and Dance Hall Crashers. The line "She brings me Mexican Food from Sombrero just because" is a reference to the Sombrero Mexican Food restaurant located in San Diego.
For the band's third music video, they attempted to take a more serious route and turned to director Jason Matzner and his collaboratorr Brendan Lambe. Hoppus' original idea was that the band would be playing on the deck of an old cruise liner as it sunk. The band would play in real time as everything around them exploded in slow motion. Gradually, the ship would reach catastrophe ("people running, sparks flying, superstructure collapsing") before the ship sinks into the dark waters as the songs ends with the line "everything's gonna be fine." As that video would have costed the band's label, MCA, millions of dollars, they settled on the alternative: the band is performing in a basement when one musician hits a pipe with his guitar, causing the room to flood. The video was shot in the backlot of Universal Studios and was director Matzner's first video. "Filming the first 'Josie' video was awful," Hoppus remembered in 2000. "We had to bring old equipment that we were willing to ruin." The trio were unhappy with the shockingly cold water, and DeLonge cut his head open on shrapnel that was floating around in water. When the band received the first edit, they decided to scrap it and start over.
The band returned to director Darren Doane, who also shot the videos for "M+M's" and "Dammit". The video stars Alyssa Milano as the girl of Hoppus' affection. "I felt really bad for her because she showed up on the set and it was just her and a bunch of perverted dudes who did nothing but stare at her breasts. They couldn't even help themselves," Hoppus recalled in 2001. The food fight scene was completed in one take by necessity, as the cafeteria was destroyed afterward. "All those kids had to sit around all day outside in the summer and, at the end of the day, they were rewarded by letting them nail us with tons of food," said Hoppus. Although "Josie" did not receive extensive MTV play, it was regardless viewed as an incredible success for the upstart band.
A clip of the original "Josie" video surfaced online in 2011.
The second video involves Mark, back at high school (filmed in Westlake Village, California at Westlake High School). The video begins with Tom skateboarding to school and is quickly met by Scott. Mark arrives with his mom dropping him off. He meets up with the rest of the band but they quickly warn him to turn around. Mark's mom gives him his lunch bag and has him kiss her on the cheek. When he turns around he notices the other kids ridiculing him. Later that day he sees Josie, (played by Alyssa Milano) a girl he likes. He proceeds to faint as she passes him by. During class, Mark writes "I Love You" on a paper airplane and throws it at Josie. Ultimately it misses and reaches a fat guy (played by Jeremy Gunther). He turns around and is shocked to see the band had thrown it; Mark and Tom point the finger at Scott, who shakes his head in denial. At lunch he sees Josie and she waves to him, but when she turns she sees a jock and quickly goes to hug him. Mark, disappointed, turns around and bumps into a large guy and a food fight ensues. Outside the cafeteria Mark notices a sign for Track Tryouts. He changes in the locker room, sees the fat guy and both scream and run away in opposite directions. Tom and Scott support Mark through the tryouts. Mark runs a race and he clears the first hurdle. He looks back and Josie is cheering him on. Mark fails the second hurdle and is comically thrown to the ground. Josie, Tom, and Scott quickly run to his aid, though apparently no one else does. On the stretcher, Josie kisses Mark right before he is loaded up, and he smiles. In the ambulance he notices the fat guy is riding with him, and screams for help to no avail.
Throughout the video, the band are shown performing in the school's lavatory, with high school-themed posters: "Go Team", "Pep Rally Friday", "School Is Cool", "School Spirit" and "We're #1". At one stage, a poster saying “Grand Moff Tarkin 4 Prez” appears at 0:54, although the name cannot be seen. This is a reference to a character in the popular Star Wars series. It appears as a result of an obsession with Star Wars shared by Mark and a member of the film crew.