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Naturally serviceable Chicago-base airlines youngest (at 23) HQ executive Sam Sullivan bends over tireless to please his colleagues, his direct boss and the grumpy big boss Russ McDonald. Sam also goes to great lengths for his no-good, almost abusive elder brother Sully. And for his first love and roommate, whose birthday he sees as his big break as she just broke up with her boyfriend Marco.
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Sam is instructed to research Sir Branson's enviably successful budget quality flight formula. He trades his first class ticket to Hongkong for two in economy, so he can take and impress 'third date' Jolie. Alas his boss turns up and cancels the plan after a mere glance inside, but Jolie has already boarded. Meanwhile brother Sully has taken Sam's car and emergency cash to start a son-soggy sandwiches business, as usual without actual planning. More surprises follow.
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Sam has got another shot to declare his love to college-crush Pieper now she's on a break with her boy-friend Marco. Alas he puts it off and is ordered to attend a crucial meeting on an ranch with French Airbus executives about buying airplanes. Worse, an accident burns his hands and hurts his 'manhood', which suffers further when embarrassment drives him to let Lizzy check 'down-there'. Ironically, his pain in the saddle proves of great value to the company.
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Sully's latest alleged shortcut to easy wealth is dog-sitting. Alas, a mean big canine swallowed a 'dog biscuit' which is actually the flash-stick containing Sam's only back-up after a power-break (also Sully's doing) for a key presentation to conclude a vital deal with a Chinese airline. Its boss, general Chen, married Sam's big boss Russ's bossy ex. For once, Meryl proves actually helpful.
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Golden boy Sam gets a promotion with raise and privileges. Alas his next job, profit assessment, discovers the staff-beloved frequent flyer program is the big money drain; Russ doesn't just trim but cut it. Piper needs an exam tutor but can' afford enough hours, so she's hell bell for Lizzi to keep seeing smart Matt as boy-friend. Sully celebrates Sam's promotion with a new jacuzzi, with surprising uses and effects for everyone.
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Now Piper is on another break with Marco, Sam bends over backwards to get her concert tickets. Alas he's needed to help prepare a deal with KLM - the big brass is too stupid to do anything properly. He even finds an error so they'll have to work the whole of Saturday night. Alas, Marco calls that he has a date, so Piper agrees to go with Derek, according to Sully for 'revenge sex'. Sam fakes an illness to sneak out. Because of car trouble he arrives after the concert, and at the after party she meets and Dandy Watholes lead-singer Courtney. It gets worse for Sam on all fronts.
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The airline needs a new market: Iceland. When Sam remarks Nordic cultures greatly appreciate hospitality, he's charged with the perfect welcome gift 'or else'. Sam also dates the new receptionist Cara, which Ross and Derek Tricolli enervate him about. Darcy orders a cool 'tusk of Aag' delivered by a junkie wrapped in newspaper, which gets him dumped with the trash. After using Mel's shower he finds only her suit. That however seems to excite Icelandic delegate Harald Juvlunktinston, so Ross orders him to date him cross-dressing. Cara doesn't believe he cancels for work. Sam gets surprising results and rewards.
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After accidentally wrecking Sam's car in the parking lot, Ross sanctimoniously spoils him, the main treat being an all-in assignment to Hawai. Ross also lends Sam his prized motorbike, which Sully accidentally wrecks indoors. To pay for a new one, Sam drags Sully to medical tests, but as addicts like Sully are barred has to swallow the drug himself. Darcy now warns about side effects from physical hell to extreme mood swings, but it's too late to cancel Hawai, and receptionist Cara accepted to go with him.
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Russ tells everybody not to buy him birthday gifts, but all executives do. After testing his interests, Sam pushes Darcy to the limit and even relies on Sully to unlawfully import a Rhodesian falcon. The gift arouses mixed memory-stirred reactions in Russ. Sam however has the even more pressing duty to return the bird after the FBI finds out and threatens to ruin his life.
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Russ decides the future depends on kids, so each board member must submit a youth-friendly new logo. Sam takes pity on his secretary Darcy, who elaborately draws horror-cartoons. To make it non-threatening, he asks lazy brother Sully, equally gifted for drawing, for a make-over. The resulting dragon wins, but then Russ spots a donut doodle Sam added and picks that. Unforytunately, Sam discovers Sully actually stile it from a well-established Luxemburg franchise.
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Sam is tickled-pink when Russ presents him to fellow airline-chiefs at a fancy lunch. Although warned by Meryl, Sam eagerly accepts to join the big boys' annual children's fund benefit traditions, but messes up his Internet donation way beyond his means. Thus unwillingly top-donor, he enjoys the royal treatment greatly, which only adds to his predicament telling Russ he can't actually pay. And then there's pay-back.
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Sam sweetly nominates Meryl for a feminist prize for successful lady air business executives, which she even wins because of his glowing essay. Ross publicly praises both of them. To Sam's surprise she's not flattered but furious ans hisses never to call her a lady. Sully has found an even dumber girlfriend, a supervisor in a cheap diner where she hires him. After a demonstration by US undersecretary for air travel security Joe Dayton of an X ray devise for virtual strip searches, both men believe Meryl is a cross-dresser. Sam is mortified when fate forces him to spend the next night in Meryl's hotel room.
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Ross orders Sam to supervise a new money making scheme: product placement, for which he hand-picks the best bid, from a bubble gum firm. Sam' initial reluctance fades after a business lunch with his equally young, female counterpart Leeza. Alas, she goes way overboard, abusing Sam's 'blank check' go-ahead. Now Ross expects Sam to undo the pilots' strike notice, which depends on persuading the dreaded union leader Pat Swanson.
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Russ demands all executives (ab)use their business acquaintances to get perks for the airline, as his late best mate and co-founder 'crazy goat' did so well. Sam risks proposing an investment scheme trough Derek Tricolli, whose cocky attitude instantly impresses Russ. Sam gets drunk and needs Sully's help to warn against Derek's actually unfair scheme, the start of more miserable humiliations.
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Russ makes fun of Sam's new assignment, calming down two fat people lobbyists. Until it goes wrong, no fault of Sam's. Nevertheless poor Sam must 'taste their fate' in a fat suit. That goes surprisingly well, except the girl who joins him in the high mile club turns out to be Russ's foxy new lover, whom he already suspects of infidelity. And the fatso's demand proof, which Russ expected, so the fat suit contained a hidden camera.
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Russ orders his major managers each to form a think-team and come up with major savings. Sam first accepts Meryl's invitation as flattering, then switches to Russ's old mate Ralph Somkin, who is about to be pensioned off. Alas Ralph is crazy enough to propose training monkeys to serve in and even fly airline planes. Ever kind Sam desperately tries to substitute his own ideas, but now seems to betray everyone.
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