1. Le poinçonneur des Lilas

In 1958 Serge Gainsbourg hit paydirt with the first song from his first album. It was not your usual chart fodder – especially in the 1950s – recounting the quotidian existence of a Metro inspector who spends his days punching holes in ticket stubs; existential angst from all 'les petit trous' leads him to contemplate putting a hole in his own head. Fast-paced, catchy and witty, Le poinçonneur des Lilas was a strong debut, though following the relatively auspicious welcome from critics and the public, he'd soon be cast into the dark again and forced to eke out a living and career that would stutter and stop/start for another decade.

2. La Chanson de Prévert

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The titular Prévert was an absurdist French poet whose poem Les feuilles mortes Gainsbourg borrowed liberally from in the making of the tune (as he also did with Paul Verlaine's Chanson d'automne). To his credit, Gainsbourg approached Prévert to ask permission to steal his words, and the two were said to have shared a rollickingly good-natured bottle of breakfast champagne together. Not knowing who the poet is shouldn't spoil your enjoyment of the song, however; it is a beautiful, elegiac waltz with pretty Spanish guitars duelling with Gainsbourg's dulcet croon; it has a hymnal, funereal feel and is unsurprisingly chosen for plenty of wakes across la Manche. Be sure of this: it'll leave a better lasting impression than You're Beautiful by James Blunt as they lower your casket into the ground.

3. La Javanaise

By 1963 Gainsbourg's career as a frontman was floundering. His star quality was in doubt, with critics cruelly rounding on his looks, paying particular attention to his ears. The writing for others was going well though, especially songs for Juliette Gréco, darling of the Rive Gauche and venerated as the thinking person's alternative to all the throwaway pop that was suddenly prevalent (much of it written by one S Gainsbourg). Her rendition of La Javanaise (a pun on a forgotten Javanese dancing craze that doesn't really translate, inspired by his mentor Boris Vian) was well received, though it is Gainsbourg's version of the moving and poetic hymn to love that has endured. Even after becoming a household name, Gainsbourg continued to write for other artists, nearly always younger women. He wrote Comment te dire adieu for Françoise Hardy and latterly a whole album for Vanessa Paradis and a Bowie tribute with a feeble franglais pun (Beau oui comme Bowie) for Isabelle Adjani. Punning is an incurable illness, and Gainsbourg's became more frequent and more deranged as his career progressed, sagging under the weight of his alcoholism.

4. Poupée de cire, poupée de son

By the mid 60s, Gainsbourg was a one man French Tin Pan Alley for the yéyé generation. And then he did his writing credentials no harm at all by winning the Eurovision Song Contest for Luxembourg with France Gall in 1965 with the song Poupée de cire, poupée de son. As a feat it was doubly impressive considering how bad her performance on the night was. This new status as an avuncular svengali brought with it responsibility, which Gainsbourg soon fiendlishly squandered. Following up Gall's success, he provided another hit with Les Sucettes. 'Annie loves lollipops …' Gall sang innocently, 'when the candy stick with anise flavour goes down Annie's throat, she is in heaven.' Despite being French, Gall clearly didn't know what a double entendre was; she was said to be devastated on finding she'd been duped by Gainsbourg, a man twice her age who probably should have known better.

5. Bonnie and Clyde

Lady Luck smiled upon Gainsbourg in late 1967 when he was not only asked to write songs for Brigitte Bardot's Christmas special Le Bardot Show, but also to be her foil, performing a number of songs to a guaranteed audience of millions. It was exposure he'd never been afforded before. If that weren't enough – and despite the fact the pair were both already married – Bardot and Gainsbourg embarked on an affair that would become tabloid fodder and do nothing to harm his reputation in the process. Legend has it Bardot asked Gainsbourg to write her the most beautiful love song he could imagine. Rising to the challenge, he wrote two. Bonnie and Clyde, inspired by the 1967 Warren Beatty and Faye Dunaway movie, is one of his best loved and most covered songs and exists within an innovative (at the time) tape loop with a bizarre yodelled exclamation that repeats throughout. The other song was Je t'aime (moi non plus).

6. Je t'aime … moi non plus

Gainsbourg's most famous song by far nearly didn't see the light of day. Recycling an instrumental track he'd tossed off for the then obscure movie Les Coeurs Verts (it has subsequently gained cult status), he wrote the erotic masterpiece with Bardot in mind, but out of respect for her faltering marriage to German playboy Gunter Sachs, she begged Gainsbourg not release the version with her on it. In desperation he's believed to have asked Marianne Faithfull, Valérie Lagrange and Mireille Darc – among others – to record the song with him but to no avail. In 1969 he met Jane Birkin on the set of the film Slogan, in which both were starring, and after a shaky start to their relationship they were soon in the studio and more pertinently an item. A ban by the BBC and the Vatican helped it sell more than 4m copies to date worldwide and precipitate a mini baby boom as the 60s became the 70s.

7. Initials BB

If Birkin was the defining relationship of Gainsbourg's life, her arrival was timely, too. Nursing a broken heart after amorous assignations with Bardot came to an abrupt end, Gainsbourg did what any other shameless, prolific songwriter would do – he wrote an album all about it. Initials BB was conceptually lamentable, though the title track is a banger. The main hook is stolen from Dvořák's New World Symphony. Gainsbourg was overtly larcenous where the classics were concerned, co-opting hook, line and sinker from Chopin for Jane Birkin's glorious Jane B. More shamefully he made what would now be called a world music album, 1964's Percussions, and lifted three songs from Babatunde Olatunji's 1959 Drums of Passion, adding his own French words but forgetting to credit Olatunji.

8. L'hôtel particulier

If Birkin had any misgivings about recording Je t'aime, she could have no doubts Histoire de Melody Nelson – Gainsbourg's chef d'oeuvre – was inspired by her (with a soupçon of Nabokov's Lolita thrown in to fan the flames of provocation). Recorded with orchestral arranger and genius Jean Claude Vannier, every moment of every one of the seven songs on the 29-minute 1971 album is sumptuous, though if we have to pick one we'll take L'hôtel particulier, which has the dirtiest groove of all. It inhabits a seedy hinterland and may have been inspired by an unnamed bordello visited by Gainsbourg and Vannier, according to biographer Darren Anderson in his recent 33⅓ book about the album.

Kate Barry

9. Je suis venu te dire que je m'en vais

Serge Gainsbourg Best Of

In 1973, Gainsbourg had his first heart attack. Forever the attention seeker, he called a press conference around his hospital bed in order to announce that he intended to smoke and drink more. If the vu de l'extérieur was a clownish facade then some of his true fears were emerging in his material, most significantly in Je suis venu te dire que je m'en vais (I came to tell you that I'm going). One of Gainsbourg's last truly great songs – of which there had been many – the expressed sentiments of regret at the ending of a fictitious relationship could just as easily be interpreted as the fears of a man suddenly deeply aware of his own mortality.

10. Aux Armes et caetera

Caroline Paulus

If, come the end of the 70s, people thought Gainsbourg was a spent force they could think again. The album Aux Armes et caetera was as welcome as it was unexpected, a collaboration with Sly Dunbar and Robbie Shakespeare that sent reggae into the mainstream in France and sold a millions copies, though not everyone was happy with a Jew reinterpreting the words of La Marseillaise aided and abetted by two black Jamaicans for the title track. The far right took issue in the press and called for Gainsbourg's citizenship to be revoked. Death threats ensued, then paratroopers crashed a gig in Strasbourg with the intention of silencing the singer, and with the threat of violence palpable, Serge sent his band home. Cutting a lonely figure on stage, he sang the national anthem a cappella. The patriots assembled could only join in and salute what was ironically intended as a chanson of rebellion in the first place. Characteristically, the scallywag had pulled victory from the jaws of defeat once again.