Homeless Sam & Sally, a 2020 dark comedy film and a television series with the same name released in 2019, is about a story regarding a mother named Sally Silver and her mentally ill son Sam Silver who comes up with ways to live normal lives while being homeless in Koreatown, Los Angeles. Dark Days, 2000, 81 minutes, documentary by Marc Singer, who followed the lives of people living in the Freedom Tunnel, an Amtrak tunnel in New York City. Homeless to Harvard: The Liz Murray Story, 2003 film about a homeless girl, Liz Murray, who works her way up to admission to Harvard University. 66 Months, a 2011 British documentary film about a homeless man who makes it on his own for 6 years without any government programs helping him. The Pursuit of Happyness, a 2006 biographical film where a father and son struggle to get a job and end up homeless after an eviction and later a tax garnishment. After several weeks living from place to place in 1981 San Francisco, he lands a permanent position in a brokerage firm after successfully completing an unpaid internship. Same Kind of Different as Me, 2017 American film about a successful art dealer, his wife and an initially violent member of a homeless shelter community. It is based on the 2006 book of the same name. Curly Sue, a 1991 comedy drama film that focuses on a homeless con artist and his friend who gets lucky with a roof over their heads by tricking a wealthy attorney.
Some see homelessness as more free than living in a house or apartment, and prefer being in nature, as well as away from other people. Some may have had a traumatic experience in a house or apartment, such as a fire, and feel safer outside, being able to survey their surroundings. Challenges
The basic problem of homelessness is the need for personal shelter, warmth, and safety. Other difficulties include:

Hygiene and sanitary facilities
Hostility from the public and laws against urban vagrancy
Cleaning and drying of clothes
Obtaining, preparing, and storing food
Keeping contact with friends, family, and government service providers without a permanent location or mailing address
Medical problems, including issues caused by an individuals homeless state (e.g., hypothermia or frostbite from sleeping outside in cold weather), or issues which are exacerbated by homelessness due to lack of access to treatment (e.g., mental health and the individual not having a place to store prescription drugs)
Personal security, quiet, and privacy, especially for sleeping, bathing, and other hygiene activities
Safekeeping of bedding, clothing, and possessions, which may have to be carried at all timesPeople experiencing homelessness face many problems beyond the lack of a safe and suitable home.