Sly Donovan was a bartender at a Malibu hotspot, the Bikini Bar. Along with his manager, Zach Hamilton, Sly met sisters Kristen and Felicia Forrester; Sly and Zach were taken with them both. Sly received a directive from Felicia's mother, Stephanie Forrester, to keep an eye on Felicia, as Felicia had almost been raped because of Zach's ties to the criminal underworld. As Stephanie was the co-founder of the prestigious fashion design house Forrester Creations, Sly obediently reported back to Stephanie when he learned Zach and Felicia planned to run away together.

As a bartender, Sly got caught up listening to the travails of Felicia's brother, Thorne Forrester, who was the center of a love triangle between his estranged wife, aspiring singer Macy Alexander, and Spencer Publications honcho Karen Spencer. When Thorne moved on with Karen, Sly sent Macy an anonymous note asking to be her date for New Year's; Sly took some heat when the disappointed Macy, who thought the note was from Thorne, berated Sly for worming his way into her life. Nevertheless, Sly became friends with Macy and tried to tell her about his growing feelings in a poem, which she laughed at. Knowing his co-worker Keith Anderson had a much better way with words, Sly had Keith write love poems for Macy, which he passed off as his own. Sly was happy when the passionate prose got Macy's attention.

Sly told Macy he'd take care of her when she started drinking heavily because her plans for a reunion with Thorne fell through. Sly gave Macy a job singing at the bar, which his customers loved. After Sly took a drunk Macy upstairs to his apartment for lovemaking, he overheard Keith telling Macy that Sly was moving too fast; Sly warned Keith not to interfere in his involvement with Macy, especially after Keith sent Macy flowers and more poems. Sly felt Macy was drinking too much and assured her worried mother, Sally Spectra, but let Macy have more alcohol when she got upset over seeing Thorne and Karen together; Sly felt that Macy would stop coming by the bar if he didn't.

Sly fumed when Keith let his little brother, Kevin Anderson, help out at the bar; Sly yelled at Kevin when he bumped into a drunken Macy and broke a tray of glasses. Sly refused to hire Kevin even after Keith told Sly that Kevin was mentally disabled. Sly covered for Macy after she moved into his apartment, watching her lie to the visiting Sally that she was sober. Sly broke up a fight between the drunk Macy and a biker chick, then panicked when Macy stumbled off to the beach by herself. Sly found Macy passed out in an alley and reluctantly agreed to let Thorne intervene. Sly sadly watched the newly-sober Macy move out, since she and Thorne had decided to reconcile.

Sly continued to object to Kevin's presence at the bar. One night after closing, Sly found himself at the mercy of a gun-wielding robber and was impressed when Kevin tackled the crook and saved him. Sly admitted he had been wrong about Kevin and gratefully hired him to work alongside Keith. Sly hosted a party celebrating Macy's sobriety, then received a call that Macy had gotten into a drunk driving accident with Kevin in the car. Sly agonized over Kevin's critical condition and breathed a sigh of relief when Kevin pulled through. Sly joined Kevin and the others visiting a remorseful Macy in the hospital, where Sly admitted that Keith had written all of "his" poems. Sly felt horrible when he was forced to fire Keith and Kevin at the bar owner's behest.

Sly struck up a friendship with the innocent, underage Jessica Forrester. Sly became jealous when he noticed Jessica's crush on Dylan Shaw, a Forrester Creations intern who was seeing Forrester model Ivana Vanderveld. Sly found out that Forrester had a "no dating the models" policy, so he went to Jessica's uncle, Eric Forrester, and reported seeing Dylan and Ivana together, which got Dylan in trouble. At Jessica's seventeenth birthday party, Sly saw that Jessica was upset over Dylan and naïvely downing Jell-O shots, so Sly got the drunk Jessica alone to seduce her, only to be stopped by Dylan, who whisked Jessica away.

Hard times fell upon the Bikini Bar with Macy no longer singing there, and Sly expressed his resentment to Dylan. Sly filled out a job application at the Insomnia Café and sheepishly defended himself when Dylan saw that Sly's given name was Irving. Soon Sly found himself under suspicion for writing Macy threatening "fan" letters which were signed by "Irv", but Sly had an alibi that cleared him of any wrongdoing. Later, with Dylan and Jessica taking things slow in a non-exclusive relationship, Sly saw Dylan kissing older woman Maggie Forrester, who turned out to be Jessica's mother, and told Jessica about it. Sly was pleased when Jessica finally agreed to go out with him. Sly also agreed to have Thorne and Macy's wedding at the Bikini.

Sly knew Jessica wasn't ready for anything heavy, yet gave her beer, took her skinny-dipping, and kissed her repeatedly. Frustrated that Jessica wouldn't have sex with him and tired of being given a hard time by his boss at the Bikini, Sly decided Jessica could be his meal ticket and proposed to her, agreeing to give Jessica time to think as long as she wore his ring. Despite his engagement, Sly fooled around with Jessica's friend, Jasmine Malone, whom he'd just hired at the Bikini. The cocky Sly even told Jasmine about his plans for Jessica, which threatened to unravel when Jessica called off their engagement; Sly barely concealed his anger as he told Jessica he would wait for her. Sly changed course and plotted to get Jessica drunk and poke a hole in a condom so he could get her pregnant and force her into marriage.

Sly took Jessica to a beach party to carry out his alcohol-soaked plan, but got so drunk himself he passed out. Sly was thrilled when Jessica informed him they'd made love and later confirmed that she was pregnant. But Sly found his path to Easy Street blocked when Jessica made him take parenting classes and train for fatherhood on a computerized baby doll that wouldn't stop crying unless Sly figured out what the "baby" needed. Sly kept trying to disable the doll, coming at it with a screwdriver and whacking it against the bar, worrying when Jessica said she would leave him if he didn't start taking his responsibility seriously.

Sly finally conceded defeat and went to Jessica to tell her he'd be a lousy father and that their baby would be better off without him. But on his way out of town, Sly changed his mind; he dressed up in a suit and tie, got an interview at a car dealership, and proudly told Jessica he was going to do right by her and the child. Sly's shock turned to outrage when Jessica told him that she knew about his plan to get her pregnant and that she'd lied about carrying his baby to teach him a lesson. Sly laughed it off but seethed inwardly when his friends made fun of him for being a chump. Sly vowed revenge and followed Jessica to the Café Russe, where Dylan had taken her for a fancy dinner; donning a mask, Sly attacked Jessica as she walked to her car, threatened to kill her, and raped her.

Sly reveled in Jessica's resultant suffering. When the skittish Jessica finally came to the Bikini with Dylan after weeks of isolation, Sly comforted his victim, who ended up arguing with Dylan. Sly asked Jessica for a dance and didn't deny it when the way he touched Jessica made her realize Sly was the one who had violated her. Sly met Jasmine for dinner at her place and laid on the sex appeal, whipping off his shirt. When Jasmine's attitude changed after seeing the birthmark on his back that Jessica had told her about, he realized Jasmine knew what he did to Jessica.

Sly waited in the back seat of Jessica's car and stopped her and Jasmine from driving to the police station, instead forcing them to go to the Bikini, where Sly tied them up. Sly ignored the girls' pleading and lorded his power over Jessica, proudly declaring that he had taken her innocence, which she could never get back. Sly scoffed when Jessica offered to get Sly help and swore she wouldn't press charges if he'd let her and Jasmine go, but Sly told them they were going up in flames, as he could get rid of them and collect insurance on the bar at the same time. As Sly started the fire, he caught Dylan untying Jasmine and Jessica and brawled with him in the bar. Sly fell onto a burning table when Dylan threw a chair at him, then burned to death after a blazing beam fell on him from the ceiling and the Bikini Bar exploded.