Inspiration From an Unlikely Source
Pairing: Jack/Liz (30 Rock) & Don/Peggy (Mad Men)
Spoilers: Through Season 4 of 30 Rock, Season 5 of Mad Men
Rating: PG-13
Disclaimer: Not mine. Jack belongs to Tina. Don belongs to Matt Weiner. I own nothing.
Basically, I treated myself to a Mad Men marathon and caught some striking similarities between Jack and Don. This is the result. Fair warning - this is my first crossover and first time dabbling in Mad Men fic. So, this may have been a huge mistake. You be the judge! Also, special thanks to lz1982 for taking the time to read this over before I posted it!
Finally, as always, feedback and comments are highly encouraged!
As much as it pains him to admit it, Lemon was right. This has to stop. The constant indecisiveness is decidedly unbecoming for man of his stature. He has to choose. Nancy or Avery. The childhood friend who still cared for him despite his less than glamorous past or the shrewd business woman who understood that deep-down, Jack Donaghy is a empty suit who really only cares about the bottom line and wants him despite (or maybe because of?) this. He can’t juggle them both anymore. He doesn’t want to.
So he has barricaded himself in his office, in an attempt to make a decision. He creates several charts and lists that details their various strengths and weaknesses. Now, there are papers strewn about the floor, several charts propped up on easels, his face illuminated by the glow of a power point presentation staring back at him from his computer screen. This is sheer madness. He forcefully closes his laptop shut and stalks over his bar and cringes when he realized that he instructed Jonathan to his alcohol away so he can concentrate. This simply will not do. He needs a drink. And a strong one.
After walking a few blocks down the street, he settles on a small and unknown bar off Madison Avenue. He has never frequented this bar before, but he figures that is just as well. He doesn’t want to risk bumping into any business associates tonight. When he sits down at the far end of the bar, he orders a cocktail made with strongest bourbon displayed on the top shelf and rubs his eyes in defeat. Women - the one aspect of his life he was never quite able to get the hang of. He could lure them into bed, sure. But the idea of a woman loving him, embracing every flawed, defective aspect of his personality and still loving him has always eluded him. He feels, though, that perhaps if he were to make the right decision about these two women, he may be able to finally enter a relationship with someone he could genuinely fall in love with. The idea is exciting and terrifying at once.
“Your Old Fashioned, sir.” The bartender says as sets the drink in front of Jack.
“I’ll have the same.” Says a man who settles himself a few seats away from Jack. Jack takes a moment to objectively appraise him and sees that he’s similarly attired in a dark, well-tailored suit. His raven black and hair and chiseled jaw reminds him of a younger version of himself. Back when he was in the bubble and even his worst flaws rarely - if ever - turned off the most stunning and beautiful women.
The man smoothly takes out a pack of cigarettes from his breast pocket and before lighting one he asks, “Do you mind?”
“You can smoke in here?”
“Last time I checked this is still a free country.” He replies with a raised eyebrow.
“Well, that certainly depends on what your definition of ‘free’ is.” Jack replies, and the man smirks in response. “Go right ahead.”
After lighting the cigarette, the young man moves one stool closer to Jack and extends his hand. “Don Draper.”
“Jack Donaghy.” When Don offers him a cigarette, Jack waves his hand dismissively. “Gave it up years ago.”
“Hmm, yes, I heard a rumor that these things kill you.” He murmurs, before exhaling.
“Everything good in life does.”
Don chuckles, “Well, that’s certainly true.” Don is about to return to his original seat, but something about his seatmate intrigues him and compels him to linger, to know more about the despondent man sitting next to him. “So, are you a lawyer?”
Jack scoffs, “God, no. I’m a television network executive.”
Don smiles, bemused. “In my line of work that’s not much better than a lawyer. I’m an ad man. You network guys have a knack for making our lives difficult.”
Jack mirrors his smirk, and lifts his drink to his lips before replying, “If it’s any consolation, Don, the feeling is mutual.” Jack downs the rest of his drink in one gulp and points to Don’s nearly empty glass, wordlessly asking if he would like another.
“Sure, why the hell not?” Don decides to make himself comfortable, and impatiently tugs at the knot of his tie. “Seems like you could use the company.”
“That obvious, huh?” Jack sighs.
“Just please tell me this is a work issue. There can’t possibly a woman out there that has someone like you so unraveled.”
Jack looks at him pointedly and confesses, “Try two.”
“Two women,” Don whistles. “Been down that road rather recently. Can’t say it’s was the most pleasant experience.”
“It’s entirely overrated.” Jack peers at him over the glass and asks, “So whom did you choose?”
Don looks like he is about to end this conversation, talking about his private life is something he rarely does, but the kinship he feels with regards to this slightly older stranger next to him is undeniable. “I had to choose between a beautiful, competent, accomplished woman. She was very much like me. Business savvy. Calculating. Knew how to reveal a person’s insecurities and use it to her own advantage…”
Jack nods in acknowledgment, “Must have been a useful asset in your line of work.”
“It certainly was. And she was exciting and invigorating…to a point.”
“What happened?”
“I wanted simplicity. I didn’t want work seeping into my home life. I wanted someone kind and uncomplicated. So, I did what many men before me have done,” he pauses, takes a sip of his drink and says, “I married my secretary.”
Jack lets out a buoyant guffaw and Don smiles in response. “So much for creativity.”
“My personal life has been very…dramatic. To say the least. I needed a break.” Don shrugs. “I’ve only encountered one other person who could offer that kind of unadulterated support and she is not an option.”
“Did you want her to be?”
He scoffs, “No.” When he sees that Jack seems unconvinced, he elaborates, “she is totally inappropriate. Awkward. Anti-social. Dresses like a sexually repressed school teacher.”
Jack smiles sadly at his ability to recognize Don’s description of this third woman and adds, “But she understands you. Probably more than anybody else has.”
A small glimpse of acknowledgement passes Don’s face, but goes away just as quickly. “She hasn’t said so to my face, but I know she judges my decision. The notion that she thinks she has a right to pass judgment on anything I do is absurd. She should be grateful for the day she came into my office. She would still be a secretary if it wasn’t for me.” Don growls angrily.
“Lemon would still walk around with lettuce in her hair, if it wasn’t for me.” Jack adds, with the same resentful tone.
“Yes!” Don nods in agreement, his hand slapping the counter. “Wait,” his brow furrows, “You call your protégée Lemon?”
Jack clears his throat, “Elizabeth Lemon. I refer to her by her last name, habit.”
“That’s impressive, Jack. Using the last name to establish just enough distance between you two. So you can come to her with your problems, but still keep things platonic, because you address her as if she was a nothing more than someone who accompanies you to the Athletic Club. Ingenious.” He sighs, wistfully. “You should have been an ad man.” Don then checks his watch, and cringes when he sees the time. “I better go. Swell meeting you, Jack.”
Jack shakes his hand, and blurts out one more question before the man leaves, “Don…Are you happy? With your decision?”
“As happy as a person like me can be.” Don replies with a sad, far away smile. He turns on his heel to leave, but swivels back around to ask, “Do you have a business card?”
Jack’s hand slips into his pocket and he retrieves his business card case. Flicking it open effortlessly, he smoothly takes one out and jots down his number on the back. “My mobile number is on the back. Feel free to call any time.”
“Mobile?” Don asks in confusion, as if Jack has suddenly slipped into speaking a foreign language. “What is that?”
Jack looks at him stunned, “My cell number.”
“I’m still at a loss.” Jack then looks around the bar, sees that the surroundings are not quite right. The phones, décor, lighting. Apparently this is not merely a retro bar emulating the style of the 60s. “Don…what year is this?”
“it’s…1967,” Don walks over to Jack, concerned over his sudden inability to grasp reality. “Are you alright, Jack?”
------
Jack is sprawled out on his couch, and Liz’s voice has finally managed to stir him awake. “Jack! Dude! Are you alright?” Jack’s eyes snap open, he lifts his head slowly, trying to carefully take in his surroundings and get his bearings. He realizes that he’s in his office, the empty bottle of whiskey on the floor beside him gives him a pretty good idea of how he got into this state. “It’s almost 9. We had a budget breakfast meeting.”
“Ah, yes, of course.” He raises his hand in the air, and Liz grabs it to help him up. He is unsteady on his feet and Liz uses all her strength to prop him up. “I just need a moment.”
“Ugh, your breath smells like a brewery. You’ll need more than a moment.”
“Thank you, Lemon. You always know how to heal my heart in times of distress.” He lets out a breath before adding, “You’ll be pleased to know that I’ve managed to make a decision amidst my drunken stupor.”
Liz quirks an eyebrow, “Is that right? So who’s the lucky gal?”
“I’m not sure whomever ends up with me will be ‘lucky,’ Liz.” He purposely walks over to the easel that displays a picture of Avery and Nancy side by side, picks it up and flings it outside of the balcony window.
“Jeepers!” Liz yelps in surprise.
“But it’s neither of them. Neither of them, will make me happy.”
“So…it’s back to square one?”
“It appears to be, yes.”
“Huh. May I ask what brought on this revelation?” Jack walks purposefully over to her, and places his hand on the familiar spot on the small of her back so he can guide her out of his office.
“Would you believe me if I said that it came from an advertising executive from the 1960s?”
“No.” She wags her head.
“Ah, well…” He opens the door with flourish and adds, “I suppose the origins of my epiphany don’t really matter. Just that I had one.”
“Yeah…” She exits his office and is about to round the corner, before she turns back around. “Hey, Jack? I’m glad you finally made a decision.” She says with a lopsided smile.
“As am I, Lemon. As am I.”
And he has the best ad man in all of New York to thank for it.
Spoilers: Through Season 4 of 30 Rock, Season 5 of Mad Men
Rating: PG-13
Disclaimer: Not mine. Jack belongs to Tina. Don belongs to Matt Weiner. I own nothing.
Basically, I treated myself to a Mad Men marathon and caught some striking similarities between Jack and Don. This is the result. Fair warning - this is my first crossover and first time dabbling in Mad Men fic. So, this may have been a huge mistake. You be the judge! Also, special thanks to lz1982 for taking the time to read this over before I posted it!
Finally, as always, feedback and comments are highly encouraged!
As much as it pains him to admit it, Lemon was right. This has to stop. The constant indecisiveness is decidedly unbecoming for man of his stature. He has to choose. Nancy or Avery. The childhood friend who still cared for him despite his less than glamorous past or the shrewd business woman who understood that deep-down, Jack Donaghy is a empty suit who really only cares about the bottom line and wants him despite (or maybe because of?) this. He can’t juggle them both anymore. He doesn’t want to.
So he has barricaded himself in his office, in an attempt to make a decision. He creates several charts and lists that details their various strengths and weaknesses. Now, there are papers strewn about the floor, several charts propped up on easels, his face illuminated by the glow of a power point presentation staring back at him from his computer screen. This is sheer madness. He forcefully closes his laptop shut and stalks over his bar and cringes when he realized that he instructed Jonathan to his alcohol away so he can concentrate. This simply will not do. He needs a drink. And a strong one.
After walking a few blocks down the street, he settles on a small and unknown bar off Madison Avenue. He has never frequented this bar before, but he figures that is just as well. He doesn’t want to risk bumping into any business associates tonight. When he sits down at the far end of the bar, he orders a cocktail made with strongest bourbon displayed on the top shelf and rubs his eyes in defeat. Women - the one aspect of his life he was never quite able to get the hang of. He could lure them into bed, sure. But the idea of a woman loving him, embracing every flawed, defective aspect of his personality and still loving him has always eluded him. He feels, though, that perhaps if he were to make the right decision about these two women, he may be able to finally enter a relationship with someone he could genuinely fall in love with. The idea is exciting and terrifying at once.
“Your Old Fashioned, sir.” The bartender says as sets the drink in front of Jack.
“I’ll have the same.” Says a man who settles himself a few seats away from Jack. Jack takes a moment to objectively appraise him and sees that he’s similarly attired in a dark, well-tailored suit. His raven black and hair and chiseled jaw reminds him of a younger version of himself. Back when he was in the bubble and even his worst flaws rarely - if ever - turned off the most stunning and beautiful women.
The man smoothly takes out a pack of cigarettes from his breast pocket and before lighting one he asks, “Do you mind?”
“You can smoke in here?”
“Last time I checked this is still a free country.” He replies with a raised eyebrow.
“Well, that certainly depends on what your definition of ‘free’ is.” Jack replies, and the man smirks in response. “Go right ahead.”
After lighting the cigarette, the young man moves one stool closer to Jack and extends his hand. “Don Draper.”
“Jack Donaghy.” When Don offers him a cigarette, Jack waves his hand dismissively. “Gave it up years ago.”
“Hmm, yes, I heard a rumor that these things kill you.” He murmurs, before exhaling.
“Everything good in life does.”
Don chuckles, “Well, that’s certainly true.” Don is about to return to his original seat, but something about his seatmate intrigues him and compels him to linger, to know more about the despondent man sitting next to him. “So, are you a lawyer?”
Jack scoffs, “God, no. I’m a television network executive.”
Don smiles, bemused. “In my line of work that’s not much better than a lawyer. I’m an ad man. You network guys have a knack for making our lives difficult.”
Jack mirrors his smirk, and lifts his drink to his lips before replying, “If it’s any consolation, Don, the feeling is mutual.” Jack downs the rest of his drink in one gulp and points to Don’s nearly empty glass, wordlessly asking if he would like another.
“Sure, why the hell not?” Don decides to make himself comfortable, and impatiently tugs at the knot of his tie. “Seems like you could use the company.”
“That obvious, huh?” Jack sighs.
“Just please tell me this is a work issue. There can’t possibly a woman out there that has someone like you so unraveled.”
Jack looks at him pointedly and confesses, “Try two.”
“Two women,” Don whistles. “Been down that road rather recently. Can’t say it’s was the most pleasant experience.”
“It’s entirely overrated.” Jack peers at him over the glass and asks, “So whom did you choose?”
Don looks like he is about to end this conversation, talking about his private life is something he rarely does, but the kinship he feels with regards to this slightly older stranger next to him is undeniable. “I had to choose between a beautiful, competent, accomplished woman. She was very much like me. Business savvy. Calculating. Knew how to reveal a person’s insecurities and use it to her own advantage…”
Jack nods in acknowledgment, “Must have been a useful asset in your line of work.”
“It certainly was. And she was exciting and invigorating…to a point.”
“What happened?”
“I wanted simplicity. I didn’t want work seeping into my home life. I wanted someone kind and uncomplicated. So, I did what many men before me have done,” he pauses, takes a sip of his drink and says, “I married my secretary.”
Jack lets out a buoyant guffaw and Don smiles in response. “So much for creativity.”
“My personal life has been very…dramatic. To say the least. I needed a break.” Don shrugs. “I’ve only encountered one other person who could offer that kind of unadulterated support and she is not an option.”
“Did you want her to be?”
He scoffs, “No.” When he sees that Jack seems unconvinced, he elaborates, “she is totally inappropriate. Awkward. Anti-social. Dresses like a sexually repressed school teacher.”
Jack smiles sadly at his ability to recognize Don’s description of this third woman and adds, “But she understands you. Probably more than anybody else has.”
A small glimpse of acknowledgement passes Don’s face, but goes away just as quickly. “She hasn’t said so to my face, but I know she judges my decision. The notion that she thinks she has a right to pass judgment on anything I do is absurd. She should be grateful for the day she came into my office. She would still be a secretary if it wasn’t for me.” Don growls angrily.
“Lemon would still walk around with lettuce in her hair, if it wasn’t for me.” Jack adds, with the same resentful tone.
“Yes!” Don nods in agreement, his hand slapping the counter. “Wait,” his brow furrows, “You call your protégée Lemon?”
Jack clears his throat, “Elizabeth Lemon. I refer to her by her last name, habit.”
“That’s impressive, Jack. Using the last name to establish just enough distance between you two. So you can come to her with your problems, but still keep things platonic, because you address her as if she was a nothing more than someone who accompanies you to the Athletic Club. Ingenious.” He sighs, wistfully. “You should have been an ad man.” Don then checks his watch, and cringes when he sees the time. “I better go. Swell meeting you, Jack.”
Jack shakes his hand, and blurts out one more question before the man leaves, “Don…Are you happy? With your decision?”
“As happy as a person like me can be.” Don replies with a sad, far away smile. He turns on his heel to leave, but swivels back around to ask, “Do you have a business card?”
Jack’s hand slips into his pocket and he retrieves his business card case. Flicking it open effortlessly, he smoothly takes one out and jots down his number on the back. “My mobile number is on the back. Feel free to call any time.”
“Mobile?” Don asks in confusion, as if Jack has suddenly slipped into speaking a foreign language. “What is that?”
Jack looks at him stunned, “My cell number.”
“I’m still at a loss.” Jack then looks around the bar, sees that the surroundings are not quite right. The phones, décor, lighting. Apparently this is not merely a retro bar emulating the style of the 60s. “Don…what year is this?”
“it’s…1967,” Don walks over to Jack, concerned over his sudden inability to grasp reality. “Are you alright, Jack?”
------
Jack is sprawled out on his couch, and Liz’s voice has finally managed to stir him awake. “Jack! Dude! Are you alright?” Jack’s eyes snap open, he lifts his head slowly, trying to carefully take in his surroundings and get his bearings. He realizes that he’s in his office, the empty bottle of whiskey on the floor beside him gives him a pretty good idea of how he got into this state. “It’s almost 9. We had a budget breakfast meeting.”
“Ah, yes, of course.” He raises his hand in the air, and Liz grabs it to help him up. He is unsteady on his feet and Liz uses all her strength to prop him up. “I just need a moment.”
“Ugh, your breath smells like a brewery. You’ll need more than a moment.”
“Thank you, Lemon. You always know how to heal my heart in times of distress.” He lets out a breath before adding, “You’ll be pleased to know that I’ve managed to make a decision amidst my drunken stupor.”
Liz quirks an eyebrow, “Is that right? So who’s the lucky gal?”
“I’m not sure whomever ends up with me will be ‘lucky,’ Liz.” He purposely walks over to the easel that displays a picture of Avery and Nancy side by side, picks it up and flings it outside of the balcony window.
“Jeepers!” Liz yelps in surprise.
“But it’s neither of them. Neither of them, will make me happy.”
“So…it’s back to square one?”
“It appears to be, yes.”
“Huh. May I ask what brought on this revelation?” Jack walks purposefully over to her, and places his hand on the familiar spot on the small of her back so he can guide her out of his office.
“Would you believe me if I said that it came from an advertising executive from the 1960s?”
“No.” She wags her head.
“Ah, well…” He opens the door with flourish and adds, “I suppose the origins of my epiphany don’t really matter. Just that I had one.”
“Yeah…” She exits his office and is about to round the corner, before she turns back around. “Hey, Jack? I’m glad you finally made a decision.” She says with a lopsided smile.
“As am I, Lemon. As am I.”
And he has the best ad man in all of New York to thank for it.