Hillside

Season 1

'Fifteen' follows the students of the fictional Hillside School and deals with a variety of issues including dating, divorce, alcohol abuse, and friendship. The show played heavily into stereotypes, including two characters named Dylan and Chris, who wore leather jackets to show off their toughness, but could not completely disguise their inner selves.

Where to Watch Season 1

13 Episodes

Checking It Out
E1
Checking It OutBrooke checks out Matt who obviously belongs to Ashley. Dylan faces off with Matt. Sparks fly. Brooke tries to flirt with Dylan, but it falls flat and she’s back to plotting with Kelly. After Courtney hems and haws, she finally drops a bombshell on Billy.
Stirring the Pot
E2
Stirring the PotCourtney confides in Jake about her parents’ problems. Matt and Ashley are doing just fine until Brooke tries to stir up trouble. Trouble is brewing for Matt with Coach Williams but we’re not sure why at first. Billy’s sucking up to Dylan until Matt interrupts.
The Dislocated Swede
E3
The Dislocated SwedeMatt and Ashley try to put the pieces back together while Brooke plots furiously. Olaf “dislocates” himself. Jake tries to get up the nerve to ask Courtney out. Matt finds Dylan talking to Ashley. Dylan lets Billy try his drums. Ashley is shocked to find Matt at the Avalon with Brooke.
True Friends
E4
True FriendsBilly and Courtney wrestle with their parents’ issues. Ashley is torn up over her doubts about Matt. Jake tries to help Matt sort things out. Courtney’s not sure it’s good for Billy to be “hanging around Dylan.” Brooke blames her dirty tricks on Kelly. Courtney thinks she has a chance with Dylan.
Free Falling
E5
Free FallingMatt takes heat from Coach Williams. Theresa bugs Brooke. Courtney falls for Dylan. Brooke can’t resist sticking her nose in again. Jake wants desperately to tell Courtney how he feels. Now Theresa fantasizes about Dylan. Courtney and Billy’s parents make it final. Ashley makes a shocking discovery..
Waiting In The Wings
E6
Waiting In The WingsMatt’s drinking raises new questions. Does Ashley dare confront him? Courtney and Billy compete for Dylan’s attention. But Jake’s in the wings wishing Courtney would notice him. Dylan’s upcoming school concert creates new tensions. Courtney surprises Brooke over at Dylan’s.
Temperature's Rising
E7
Temperature's RisingMatt gets benched. Brooke brags to Kelly how she upstaged Courtney with Dylan. Billy can’t find anyone to talk to but Olaf. Courtney asks Ashley for advice. Matt tries to start a fight with Dylan. Matt hides a problem at school and Ashley confronts him. Courtney’s fantasy life flourishes.
Lean On Me
E8
Lean On MeAshley leans on Jake for help with Matt but how’s he supposed to help. Courtney provokes a fight with Dylan. Cyndi and Olaf’s attempts to save the environment meet with a feeble response at Hillside. Courtney makes up with Dylan and she and Billy plan to throw a party. Naturally, Brooke tosses a grenade into the plans and Jake has to pick up the pieces.
The Green-Eyed Monster
E9
The Green-Eyed MonsterBilly defends his dad with Courtney. Jake confides in Ashley. Matt makes fun of the “Environmental Police,” while Brooke uses the cause for her own ends. Billy isn’t sure whether to be friends with Olaf. Dylan’s concert is cancelled and Billy is responsible. Ashley’s feeling sorry for Dylan makes Matt jealous.
The Party
E10
The PartyMatt’s tension with the Coach worsens and, unlikely as it is, Matt tries to give Jake romantic advice. Olaf has a theory about Bart Simpson. Jake tries a new approach with Courtney. Brook pursues her ambition to be Student Council President. Ashley tries to help Matt but Matt hits a wall with the coach. The Party at Courtney and Billy’s ends with a shock.
Damage Control
E11
Damage ControlThere’s a need for damage control after the Party but Brooke still has her eye on the election. Matt and Ashley have different takes on his “falling down drunk.” Jake finally asks Courtney out and tries to help Ashley with Matt. Cyndi gives Dylan some advice. Ashley wants to help Matt but Brooke manages to get there first.
Hanging In the Balance
E12
Hanging In the BalanceAshley and Matt’s relationship is on the rocks. Matt loses his patience with Jake and their friendship is put to the test. Brooke pretends to sympathize with Ashley. Courtney rejects Dylan’s attempts to make up. Ashley cheats on a test and Brooke and Kelly are quick to rub it in. Billy gets back in with Dylan.
The Worm Turns
E13
The Worm TurnsEveryone’s worried about Ashley and her parents are about to ruin her life. Brooke ramps up her campaign for Student Council President. To help matters, Kelly starts flirting with Dylan. Billy does a double take when Theresa takes an interest in him. Dylan surprises Billy with a major offer. Jake hasn’t given up on helping Matt. Kelly sets Brooke up for a fall. Dylan’s determined to build up his band.