Can't remember which song was playing when Da Gang strode out to the car in Two Cathedrals? Want to know the lyrics CJ lip syncs when she does The Jackal? Welcome to Ryo's Land of Popular Music!

Side B
I Don't Like Mondays
Written by the Boomtown Rats, Performed by Tori Amos - Strange Little Girls, 2001
After a brief discussion between Josh and Donna about this song's origins -- a comment by a high school girl who shot up her school -- Tori Amos's transcendent version plays in the background as the West Wing staffers learn of a terrorist attack on American soil.  CJ fields questions in her briefing, Toby, Josh, and Donna watch the breaking news in silence, Leo sends Margaret to get him information, and Jed Bartlet delivers an eloquent and resonant speech while this song plays on [4.2].
Though CJ Cregg doesn't know the words to I'm Too Sexy -- and has to ask her assistant, Carol, what the song means -- that doesn't stop her from wandering the halls of the West Wing singing. In fact, she substitutes lyrics of her own making when she can't remember the original ("I'm too sexy for my shirt, too sexy for my skirt, too sexy for the other thing…"), much to Toby's amusement. While this is no performance of The Jackal, it certainly is memorable [3.6].
Although CJ claims not to know how, she agrees to play pool with Toby for money. During the game, Toby -- in his inimitable Tobyesque way -- remarks that Leo's told him "what you're thinking about doing." CJ doesn't reply (and later rebukes Leo for sharing their conversation with Toby) neither confirming nor denying whether she's considering resignation, but she seems to appreciate Toby's roundabout way of showing support. And all the while, the wistful strains of Instead play in the background [3.1].
During times of celebration, CJ Cregg can sometimes be persuaded to "do The Jackal," which is greeted by her coworkers with much anticipation, applause, and laughter. Leo says he "loves it," Toby admonishes Sam with "Don't ever talk to me during The Jackal," and Sam himself says that "if you haven't seen CJ do The Jackal, then you haven't seen Shakespeare the way it's meant to be done." And the performance is worthy of such high regard: CJ turns on Ronnie Jordan, lets down her hair, lip syncs to the lyrics, and sashays and shimmies around the room [1.18].
Joy to the World
Composed by George Frideric Handel, performed by John Fenstermaker - A Brass & Organ Christmas, 2000
After being accused of not being in the holiday spirit in years past, Toby Ziegler takes it upon himself to fill the entryway of the White House with festive music, damn it.  Among his choices -- a brass quintet performing Joy to the World, which does little for Josh Lyman's frayed nerves [2.10]
On the President's instructions, Josh Lyman agrees to take Charlie Young out for a beer after work. Josh asks Sam Seaborn to join them, but what he isn't counting on is the fact that Mallory O'Brien, Zoey Bartlet, and CJ Cregg invite themselves along.; As Josh succinctly puts it, "The President's daughter, the Chief of Staff's daughter, a Georgetown bar, and Sam.  What could possibly go wrong?" Quite a bit, as it turns out, and it all happens to the accompaniment of the Foo Fighters' peppy Learn to Fly [1.6].
As the President and the majority of his staffers watch a choral group perform at the White House, Toby Ziegler and Mrs. Landingham attend the funeral of a homeless veteran at Arlington Cemetery. Toby, who became involved when his business card was found in the jacket pocket of the dead man, arranged the funeral by using the President's name, and after admonishing him, Mrs. Landingham asked to accompany him -- she lost her two sons in Vietnam one Christmas Eve. The last moments of the episode are without dialogue, and the action cuts back and forth between the honor guard at Arlington and the staffers assembling in the West Wing, all to the haunting strains of this popular Christmas Carol [1.10].
After winning re-election, Jed and Abbey settle in for the night in the Residence.  As Jed mixes some Stoli Martinis of Seduction and blathers on at some length about the humid bayou of Louisiana, Dean Martin's Love Me, My Love plays on [4.8].  
Jed Bartlet, while contemplating Leo McGarry's suggestion for the Congressional Democrats' response to his official censure, sits in the Oval Office, absently singing Makin' Whoopee.  When he stops singing abruptly, Charlie Young supplies the next line, "Yeah, the line you're looking for is 'Another sunny honeymoon'" [3.16].
After an incisive comment from Will Bailey, the President retreats to the Residence to do some work and ponder what can be done about the genocide in Kundu.  The current foreign policy dictates that America not intervene for purely humanitarian interests.  However, Jed Bartlet, while watching footage of American soldiers on CNS and part of the Laurel & Hardy movie Babes in Toyland comes to a decision:  that streak's gonna end at noon on Sunday when he announces a new foreign policy in his second Inaugural Address [4.15].
Moment of Weakness
nbsp;Bif NakedI Bificus, 1999
When we first meet Mandy Hampton, she's careening along in her BMW convertible and arguing on her cellphone.  Just before she gets pulled over by the motorcycle cop for blowing through a red light, the song blaring from her car stereo is Moment of Weakness [1.1].
In We Killed Yamamoto, we learn that Amy Gardner is quite fond of Van Morrison.  This is the other song that's playing in the episode.  You know, right before the cellphone is tossed into the stew [3.21].
As Leo relays to the president that the man who saved his life in Korea has failed to comply with the law in order to win a defense contract, Bartlet's copy of My Country 'Tis of Thee plays hauntingly in the background [5.14].
National Emblem March
Written by E. E. Bagley, performed by the Boston Pops - God Bless America, 2002
Before the President takes the podium to address members of the Navy at Naval Warfare Center Crane, the band plays National Emblem March [4.1].
Three days after finding out his father has been having an affair for the past 28 years, Sam Seaborn awakens to the strains of Don Henley's New York Minute, still in yesterday's clothes and still in the office (Toby's office, to be precise, since Sam doesn't have a couch in his). Sam, who has been knocked off his game by his father's revelation, wades through the day -- which happens to be Leo's Big Block of Cheese Day -- on little sleep and less patience. With Donna's help, he pulls himself together and agrees to Josh's plan ("We're going to get Sam drunk and put him to bed"), but first he makes a phone call to his father, as New York Minute swells in the background. Notably, the title of this episode -- Somebody's Going to Emergency, Somebody's Going to Jail -- is culled from the song's lyrics [2.16].
After the First Lady realizes she may lose her license, she gathers CJ Cregg and lobbyist Amy Gardner to join her to, in her words, "get drunk." They retreat to a small room, and are later joined by Donna Moss, who is unsure of her citizenship due to the American-Canadian border being redrawn. Abbey is snapped out of her self-pity mode by an unthinking yet utterly sensible remark by Donna, and as a thank you, Abbey has the band play O Canada [3.15].
At the end of Holy Night, as Josh and Leo keep each other company, Will remains hard at work surrounded by Sam Seaborn for Congress posters and stray bicycles, CJ and Danny work on opposite sides of the story, and Jed Bartlet broods in the Oval Office, Toby stands with his estranged father Julie in the Northwest Lobby as the Whiffenpoofs perform a transcendent version of O Holy Night [4.11].
The Barenaked Ladies perform (and by "perform" I mean that the CD version of the song blasted through the speakers while the BNL boys jumped around on stage) their breakthrough tune, One Week, at a Rock the Vote rally emceed by Ms. Claudia Jean Cregg, sporting a lovely pair of jeans and a Rock the Vote t-shirt.  Meanwhile, Josh and Toby huddle at a table on the balcony crunching the numbers for their ideal tuition tax credit [4.3].
At the end of Sorkin's fictitious play-within-a-play--The Wars of the Roses--that President Bartlet and his entourage attend, a song from the actual play, Nicholas Nickleby, is used. Perhaps the song is meant as ironic commentary, as it plays over the decision Bartlet makes to order the summary execution of Shareef [3.22].
As the President arrived on the dais to deliver his commencement address at Zoey's graduation, that old commencement classic, Pomp & Circumstance, was played by the band [4.22].
After a lengthy physical recovery, Josh Lyman jumped right back into the swing of things at work -- only it seems he neglected to deal with the emotional aftereffects of nearly dying at the hands of racist thugs.  As Josh's (as yet undiagnosed) Post-Traumatic Stress Disorder worsens, he attends the Congressional Christmas party to hear Yo-Yo Ma play. The music triggers Josh's worst flashback yet, and later that night, he puts his hand through a window in a vain attempt to make it stop. Later when Josh recounts the events to Stanley Keyworth, a psychologist with ATVA, he says, "It was the Bach in G Major" [2.10].
After Toby's Day of Jubilee, he arrives at the White House in uncharacteristically good spirits.  In fact, he freaks Margaret out by telling her to let her smile be her umbrella.  Then in a moment of utter strangeness, Toby sings a line from Put on a Happy Face [1.18].
When Josh Lyman's plan to go to Tahiti for the weekend with quasi-girlfriend -- and pseudo-feminist -- Amy Gardner is foiled, he decorates his Georgetown home in a tacky Tahitian theme. Co-opting Donna Moss into his scheme, Josh lures Amy there, and the viewing audience is subjected to Josh and Amy kissing to the sounds of Red, Red Wine [3.12].
While CJ is off learning that Danny screwed her and someone on one of their staffs screwed the rest of them, Toby and Josh continue the conversation about genocide and their responsibility to do something to stop it.  As Josh points out, if America had been the world's police back in the thirties, they'd both have a lot more relatives.  Meanwhile, Jill Sobule is performing this plaintive song on the stage [4.15].
Rock the Boat
Hues Corporation - Rock the Boat: Golden Classics, 1993 (song originally recorded in 1974)
The funky sounds of Rock the Boat don't seem conducive to concentration, but nevertheless, Sam is sitting in a bar rewriting the President's announcement speech -- which is a major bone of contention between Bartlet's staff, and Bruno's band of hired guns -- as the Hues Corporation's biggest hit grooves on in the background. CJ, meanwhile, is drawing inspiration from Hunter John and the Goff family -- until she reads that their family owned and operated mill burned down in the late 1800s [3.1].
It's been sixteen hours and Zoey Bartlet's still missing.   Jed, Abbey, Elizabeth, Ellie, and Charlie head for a private mass, Josh and Donna stop on the sidewalk outside the White House, awed by the outpouring of support for Zoey in the form of candles, signs, and flowers.  Inside, Acting President Walken monitors a military response to the crisis that may doom Zoey [5.1]
There's a rumor floating around in West Wingland that the song playing in Mandy Hampton's car just before she attempts to run down Lloyd Russell with her BMW is She's Lost Control.  However, I have not yet narrowed down which version matches what we can hear in the episode [1.2].
Shed a Little Light
Written by James Taylor, performed by Aimee MannNew Moonshine [James Taylor], 1991
At the Rock the Vote rally in what CJ calls the "labor delivery room of American Democracy"--Massachusetts--Aimee Mann performed James Taylor's plaintive political song.  During which Josh and Amy have a strange conversation about Stackhouse, the third party candidate who wants into the Presidential debates [4.3].
Silver Bells
Written by Jay Livingston and Ray Evans, performed by Bing Crosby -- White Christmas, 1992.
On December 23, 1954, somewhere in Brooklyn Heights, someone is watching a performer on TV singing Silver Bells.  If anyone recognized the singer's voice (Bing Crosby?), feel free to let me know [4.11].
As Leo McGarry attempts to romance Jordan Kendall with exit poll demographics on election night, they dance on the Portico to Gershwin's Someone to Watch over Me [4.8].
Suite for Orchestra No 3 in D Major (Air on a G String)
Composed by Johann Sebastian Bach, conducted by Neville Mariner - Bach: Orchestral Suites & Violin Concertos, 1995
When Sam Seaborn goes down to the basement to talk to Ainsley Hayes about the liability shield he helped draft for the now leaking oil tanker, she's busily working, classical music on in the background.  Sam asks about the song, but doesn't let her answer him, because he believes he knows the title. Mostly because of the phrase "G String" [2.20].
Although Josh successfully sang a line from The Music Man, apparently he's not up on his Rodgers & Hammerstein.  While trying to recall the only song the piano player at the Wilson knew, he tried Little things with fur better hurry which should, of course, be Chicks and ducks and geese better scurry.  Don't worry; Donna sets him straight [3.11].
After Jed Bartlet gives his victory speech and exits the stage, Bob Dylan's The Times They Are A-Changin' cranks out over the loudspeakers.  Though it seems an odd choice for a re-election campaign, perhaps it was the campaign song for the original Bartlet for America campaign [3.7].
The Wanderer
Dion - Runaround Sue, 1993
As a disgruntled Toby Ziegler and a grumpy Josh Lyman continue to argue over whether winning the election is the same thing as beating their opponent, Donna Moss grows increasingly frustrated with their antics.  The music playing in the small, dark bar just before she sets them straight is, rather appropriately, The Wanderer [4.2].
We Gather Together
The Cedarmont Kids - School Days, 1995
CJ Cregg's second Thanksgiving as White House Press Secretary is quite a strange one.  Aside from the two turkeys taking up temporary residence in her office, orchestrating the official turkey pardon, and cajoling the president into drafting the remaining turkey into the military, CJ must also lead children in song.  Live on CNN.  Sadly, we don't get to see the scene, but we do hear a bit of the children singing We Gather Together at the end of the episode [2.8].
We Three Kings
The Irish Tenors - We Three Kings, 2003
As Jed and his grandson, Gus, light and relight the White House Christmas tree, this familiar holiday classic plays [5.8].
The Wells Fargo Wagon 
Written by Meredith Willson, performed by the original Broadway cast - The Music Man
In response to Donna Moss's questions about why America was willing to bail out the faltering Mexican economy, Josh Lyman sets off for a meeting singing a couple lines of The Wells Fargo Wagon.  Who knew he was a fan of musicals? [2.19]
Toby Ziegler hired, among other groups, the Duncan McTavish Clarney Highland Bagpipe Regimen to play holiday music in the Northwest Lobby.  Josh Lyman, whose Post-Traumatic Stress Disorder is triggered by music, confronts Toby, complaining that he can hear the "damn sirens all over the building," then shouts at the people in his bullpen, alarming both Toby and CJ [2.10].
Won't You Come Home, Bill Bailey
Words and Music by Hughie Cannon (source:  Duke), performed by Bobby Darin - Very Best of Bobby Darin [IMPORT]
As Sam makes his way to the phone to take a call from Will Bailey on Election Day, he sings a few lines of Won't You Come Home, Bill Bailey [3.7].
When Jed and Abbey arrive home from Church, they walk down the portico toward the entrance to the White House while Jed sings Frank's timeless You Make Me Feel So Young to Abbey [3.5].
Much thanks to Jo March, Margeurite, Kat, Lisa R., Kimberly, Brian, Dana, Ginny, Anne, Stargirl, Julia, Marina, KDTB, Abby Dan, and Kasey for providing timely answers, song titles, and information.

The wwwhores have a page of music from The West Wing as well.