The worlds of criminal justice and filmmaking entertainment overlap repeatedly in the disturbing documentary “Aileen: Life and Death of a Serial Killer” (9 p.m., HBO), from controversial director Nick Broomfield (“Kurt & Courtney”).

This is Broomfield’s second film about Aileen Wuornos, the executed convicted serial killer immortalized on the big screen by Charlize Theron’s Oscar-winning performance in the 2003 drama “Monster.” Broomfield covered Wuornos’ 1992 arrest and several trials in “Aileen Wuornos: The Selling of a Serial Killer,” a film that revealed her inept (and frequently stoned) lawyer as well as efforts by her attorney and several police officers to profit from Wuornos by selling her story to Hollywood.

Broomfield returned to the story when he was subpoenaed to appear at her last appeals trial before her execution. “Aileen” includes revealing and ultimately contradictory interviews with Wuornos. At one point she recants her stories of killing seven men in self-defense and declares that the murders were premeditated. Later she tells Broomfield that she only said that to speed up the date of her execution.

The film’s most harrowing scenes occur when Broomfield returns to the Detroit suburb where Wuornos was raised in grim conditions. Abandoned at birth by both parents, she grew up with an abusive grandfather. Neighbors attest to frequent and severe beatings and an incestuous relationship with her brother. Aileen began trading sex for favors and cigarettes at an early age. After a pregnancy she was banished to the woods at the edge of town, where she lived in a self-made fort and turned to prostitution for survival. She was 13.

The film also includes news footage of Broomfield discussing the case with reporters and revealing a clear point of view. “I just formed the opinion that here was somebody who has obviously lost her mind, has totally lost touch with reality. We are executing a person who is mad. I find it very disturbing.”

Tonights other highlights

• Repeats of “Late Night with Conan O’Brian” (6 p.m.) will now air nightly on CNBC. I’ve always thought of Conan as “all business.”
• Group therapy on “Everybody Loves Raymond” (8 p.m., CBS).
• Ed meets a blast from his past (Alec Baldwin) on “Las Vegas” (8 p.m., NBC).
• The Dallas Cowboys host the Philadelphia Eagles on “Monday Night Football” (8 p.m., ABC).
• A speed-dater rushes to his death on “CSI: Miami” (9 p.m., CBS).
• “Retrosexual: The ’80s” (9 p.m., VH1) devotes five hours over five nights to the peculiar proposition that the 1980s were sexy.

Series notes

A cruise to forget on “Still Standing” (7 p.m., CBS) … Joe Rogan hosts “Fear Factor” (7 p.m., NBC) … Women swap homes on “Trading Spouses: Meet Your New Mommy” (7 p.m., Fox) … George Hamilton hosts “Life of Luxury” (7 p.m., ABC).

Mobile-phone lessons on “Listen Up” (7:30 p.m., CBS) … A boyfriend with baggage on “Half & Half” (7:30 p.m., UPN).

Two transformed sisters on “The Swan” (8 p.m., Fox) … A medical near-miss on “Girlfriends” (8 p.m., UPN) … James Earl Jones guest stars on “Everwood” (8 p.m., WB) … Lance Bass guest stars on “$25 Dollar Million Hoax” (9 p.m., NBC).

Late night

Jerry Seinfeld and Jamie Oliver appear on “Late Show with David Letterman” (10:35 p.m., CBS) … Jay Leno hosts George Carlin, Denise Richards and Lenny Kravitz on “The Tonight Show” (10:35 p.m., NBC) … Tommy Lee and Tony Perkins appear on “Jimmy Kimmel Live” (11:05 p.m., ABC).

Tom Hanks, Sam Moore and Carla Thomas chat on “Late Night with Conan O’Brien” (11:35 p.m., NBC) … D.L. Hughley hosts Andrea Bocelli on “The Late, Late Show” (11:37 p.m., CBS).