Two weeks after Joshua Lipton was charged in a drunken driving crash that seriously injured a woman, photos of the 20-year-old college junior showing him in a black-and-white striped shirt and an orange jumpsuit labeled "Jail Bird" showed up on Facebook.

Jay Sullivan, the prosecutor in Lipton's case, used the photos -- taken at a Halloween party -- to illustrate to the judge that Lipton was an unrepentant partier who was out having a good time while his victim recovered in the hospital. The judge agreed, calling the pictures depraved when sentencing Lipton to two years in prison.

Online hangouts like Facebook and MySpace have offered crime-solving help to detectives and become a resource for employers vetting job applicants. Now the sites are proving fruitful for prosecutors, who have used damaging Internet photos of defendants to cast doubt on their character during sentencing hearings and argue for harsher punishment.

    "Social networking sites are just another way that people say things or do things that come back and haunt them," said Phil Malone, director of the cyberlaw clinic at Harvard Law School's Berkman Center for Internet & Society. "The things that people say online or leave online are pretty permanent."

    Rhode Island prosecutors say Lipton was drunk and speeding near his school, Bryant University in Smithfield, in October 2006 when he triggered a three-car collision that left 20-year-old Jade Combies hospitalized for weeks.

    Sullivan, the prosecutor, said another victim of the crash gave him copies of photographs from Lipton's Facebook page that were posted after the collision. Sullivan assembled the pictures — which were posted by someone else but accessible on Lipton's page — into a PowerPoint presentation at sentencing.

    One image shows a smiling Lipton at the Halloween party, clutching cans of the energy drink Red Bull with his arm draped around a young woman in a sorority T-shirt. Above it, Sullivan rhetorically wrote, "Remorseful?"

    Superior Court Judge Daniel Procaccini said the prosecutor's slide show influenced his decision to sentence Lipton. "I did feel that gave me some indication of how that young man was feeling a short time after a near-fatal accident, that he thought it was appropriate to joke and mock about the possibility of going to prison," the judge said in an interview.