Season Eight brings a return to bachelordom for Charlie Harper (Charlie Sheen) as TV’s #1 comedy finds its hilarious form once more. Add in the amorous blunders of Charlie’s divorcee brother Alan and the lovable, but sometimes cement-headed decisions of Charlie’s teenaged nephew Jake and these (almost three) men add up to riotous fun!
On the eighth season premiere, Jake (series star ANGUS T. JONES) finds out that Alan (series star JON CRYER) has been dating Eldridge's mom (recurring guest star COURTNEY THORNE-SMITH), so he packs up and heads to Judith (series star MARIN HINKLE) and Herb's (recurring guest star RYAN STILES). Meanwhile, Charlie (series star CHARLIE SHEEN) decides it's time to cut back on boozing.
When Lindsey asks Alan to move in with her, Charlie will do anything to get Alan to say "yes!
Alan moves in with Lyndsey but continues to have a rendezvous with Melissa at Charlie's house.
Lyndsey and Eldridge move into Charlie's house after Alan burns down their home. JUDD NELSON (Suddenly Susan, St. Elmo’s Fire) guest stars as Lyndsey’s ex-husband.
Alan goes out on the town pretending to be Charlie while Charlie sneaks off for some cosmetic surgery.
Charlie has trouble adjusting to dating a slightly older woman (guest star LIZ VASSEY – CSI: Crime Scene Investigation).
Charlie's past comes back to bite him when his girlfriend (Liz Vassey) decides that his longtime stalker, Rose (guest star MELANIE LYNSKEY), is just too much to handle.
Charlie and Alan try to set up their mother with Russell, the pharmacist (returning guest star MARTIN MULL).
When Berta takes a couple of days off, Charlie falls for her replacement (guest star TONITA CASTRO). Meanwhile, Alan believes he's being stalked by Lyndsey's ex-husband. Courtney Thorne-Smith returns as Alan’s former girlfriend, Lyndsey and Judd Nelson returns as her ex-husband.
Charlie goes on a spending spree for his old fling, Courtney (guest star JENNY McCARTHY), who shows up after three years in prison for conning him out of money. Guest star CARL REINER returns as Marty, Evelyn’s old fling.
Alan is ashamed that he can't afford to buy Lyndsey a birthday present, so he gets creative. JENNY McCARTHY returns as Charlie’s girlfriend.
When Charlie and Courtney break up, Charlie falls into a depression and goes to see his psychiatrist, Dr. Freeman (guest star JANE LYNCH).
When Charlie and Lyndsey start becoming friendly, Alan’s paranoia gets the best of him.
Charlie's obsession with the newly "married" Rose leads him to stalk her. Meanwhile, Alan grows concerned when Jake and Eldridge start videotaping stupid and extremely dangerous stunts.
In an attempt to grow his business, Alan inadvertently starts a Ponzi scheme using his friends and family as investors. Charlie’s love for Rose only deepens as they continue their torrid “affair.”
Rose uncovers Alan's Ponzi scheme and Alan, in turn, meets "Manny," Rose's mannequin "husband." Meanwhile, Charlie is eager to get some alone time with Rose.