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  There was one kid at Ann Arbor High who back in 1965 was undoubtedly aware of this brutal truth; one kid who had a burning belief in himself, and a fierce desire to succeed, and that was Jim Osterberg, the boy who’d finessed his way so often, but only ever to second place. But still he knew that he was special. He would get to first place in something. All he needed to do was find out what it was.

  CHAPTER 2

  Night of the Iguana

  The most respected guru of Chicago’s blues and jazz scene hadn’t expected this cold winter evening would turn out to be such an ordeal. A champion of black music, the patron of fast-rising young blues turks like Magic Sam and Junior Wells and the owner of Chicago’s hippest record store, Bob Koester generally found that even the most ornery musicians would treat him with affection, or at least respect. But tonight, one of the most engaging, intelligent musicians he’d ever encountered was out to torture him, and soon he would find the limits of his endurance.

  From the moment Koester had met Iggy Osterberg, he had been charmed by the young drummer’s intelligence and enthusiasm. He was sufficiently enthused by the aspiring blues drummer to hire him for a gig with bluesman Big Walter Horton, who was playing a demonstration set at Oak’s Park swanky Frank Lloyd Wright-designed Unitarian Temple, to accompany a talk by Koester on the blues in front of an admiring, middle-class audience. Iggy had acquitted himself well musically, while his tact and intelligence were demonstrated by the way he’d charmed some of Chicago’s toughest bluesmen. But on this cold evening, at Koester ’s apartment on the ground floor of 530 North Wabash, in the winter of 1966, that charm had disappeared. In its place was malevolence.

  It had all started when Iggy had asked Koester, who’d been putting him up for a week or so, if some of his friends could drop by. His friends were what Koester termed ‘psychedelic dudes’, but there was little peace and love in the vibe they brought. Of the five of them, Vivian Shevitz was OK, but now she’d disappeared in search of her friend Sam Lay, who was in hospital after accidentally shooting himself in the scrotum. The Asheton brothers, Ron and Scott, were a nasty pair; Ron’s party-piece was a Gestapo interrogation routine, where he’d shine a light into Koester’s face while sneering, ‘Ve haf vays of making you talk.’ Scott was more physically intimidating, a handsome, broody youth who resembled a young Elvis Presley and seemed to enjoy playing frisbee with Koester’s precious blues 78s. The fourth psychedelic dude, Scott Richardson, was a Jagger-lookalike singer who professed to like Howlin’ Wolf, but he was equally indifferent to Koester’s blues guru status. He joined the others in taunting him, wrestling with each other, walking round the apartment shouting, mocking Koester or laughing at Iggy - or Ego, as Koester had started to nickname him - as the drummer danced naked with his dick folded back between his legs, shouting, ‘I’m a girl, I’m a girl!’

  By now, the headache that had been coming on over the evening made Koester feel like his skull was clamped in a vice, and his young charges were cranking up the pressure. Cradling his head in his hands, he asked Iggy if he could pour him a glass of water. For once, Iggy seemed sympathetic, and headed for the bathroom with a glass. Reappearing, he passed the full glass to Koester, who raised it to his lips before the warmth and retch-inducing reek of its contents alerted him. The little shit was trying to get Koester to drink a glass of piss! Enraged, Koester threw the glass at Osterberg, who held up his hand to protect himself as the glass shattered, cutting his finger and splattering its contents over the apartment. Incandescent with rage, Koester screamed at the young fucks to get out, bundling all of them out of the door and into the freezing Chicago night.

  As they walked round the Loop in search of an all-night cinema, Iggy seemed strangely unconcerned. Teeth chattering, he confided to Ron Asheton that he’d abandoned his ambition of being a blues drummer. He wanted to form a band. And he wanted Ron and Scott to join him. He had an idea that they could come up with something different.

  It was the drums that called James Osterberg away from politics. Trained in the school marching band, he later graduated to the orchestra proper, and right around the time the first stirrings of rock ’n’ roll reached Michigan, he enrolled in a school summer camp and brought his marching-band side drum with him. One morning the seventh and eighth graders were being called from their dormitories to the assembly area, and Jim took it upon himself to lead them through the tree-lined paths, like a paradiddling Pied Piper: ‘Jim was playing really, really well, and the kids just lined up and started marching,’ says Denny Olmsted. ‘He didn’t have a shirt on and looked really healthy and fit; he had a flat-top haircut, like all of us. It sounded great, and everyone just followed him in formation and marched down the path.’

  It became a ritual that was repeated over several consecutive days. And whatever his ambitions of emulating John F. Kennedy via his ample gift for public speaking, it was with this basic, primal beat that Jim Osterberg first became a leader.

  Over subsequent months, visitors to the Osterbergs’ trailer, like Brad Jones, noticed he had acquired a drum practice pad - modest circles glued to a piece of plywood - but it wasn’t until 1961 that Osterberg, then fifteen, had his first brush with rock ’n’ roll, after he met up with, he says, a ‘not particularly popular, not particularly anything, but nice’ kid called Jim McLaughlin, in the school marching band. McLaughlin’s dad was a radio tinkerer, like a local Leo Fender, whose house on Hermitage, near Tappan, was always littered with microphones and amplification equipment, and it was there that Osterberg first heard Duane Eddy, Ray Charles and Chuck Berry. ‘And I was like, Holy Christ, this is some serious shit.’

  McLaughlin became Osterberg’s closest friend, and the two spent long hours after school at the trailer in Ypsilanti, McLaughlin working out boogie riffs on guitar and Osterberg accompanying him on his tiny three-piece drum kit. An intelligent, unassuming man who now works in trade exhibitions, to this day McLaughlin is impressed by his childhood friend’s confidence and his ‘utter fearlessness’. He was also taken aback by the fierce rivalry between the Osterberg males: ‘They had the most incredibly adversarial relationship in the world, they were at each other’s throats every second - oneupmanship, who could cut the other person down, who had a quicker wit. They would take golf trips down to North Carolina, play every day and just go to war. It was such a paradox, because the guy also inherited this literary interest from his father and obviously the golf and the athletics, too.’

  McLaughlin was nervous about the rock ’n’ roll duo’s public debut, but his new bandmate talked him into playing at a Tappan Talent Show in March 1962; they played two numbers, Sandy Nelson’s ‘Let There Be Drums’, and then a self-written 12-bar using a bunch of Duane Eddy and Chuck Berry cast-off riffs. Introduced as the Megaton Two by Osterberg’s friend Brad Jones, they took to the stage, and their rendition of Nelson’s drum showcase aroused a decent spattering of applause. By the second number, ‘People went nuts, they were dancing in the aisle, the teachers were running round telling ’em to sit down,’ says McLaughlin. After the show, one of the high-school jocks went up to the drummer and gruffly congratulated him. ‘“Hey, Osterberg, that sounded good, your band’s pretty cool,” sorta thing. And girls liked us a little bit. And that was how it started off.’

  As casual as it was, that jock’s comment, the first modest acclaim, together with the subtle approval of Tappan’s schoolgirls, would launch a fateful career - one in which future audiences’ responses would veer from rapture to violence. It would be another two years before Osterberg’s musical ambitions took obvious priority over his status as a classroom politician, but there was a good reason for the switch. As a politician, Osterberg relied on his verbal facility, his reading of audiences and his sheer audacity. Every one of those skills was also vital to his musical career, which demanded sustained hard work too, but music would become the one pastime he loved for itself, rather than for its ability to impress others.

  From now on, he would practise incessantly with Mc
Laughlin after school, and when the pair moved up to Ann Arbor High the work intensified as the line-up was augmented with sax-player Sam Swisher, the son of an Ann Arbor real-estate agent who lived over the road from the McLaughlins, and, in 1964, bassist Don Swickerath and guitarist Nick Kolokithas, who knew McLaughlin via a local guitar teacher, Bob Richter. Osterberg named the band the Iguanas, after what he claimed was the ‘coolest’ animal, and over the following two years, as they played the local high schools and frat parties at the University of Michigan, their set changed in tune with Michigan’s musical vibe, with frat-band sax-led songs like ‘Wild Weekend’ or ‘Walk, Don’t Run’ being supplanted by numbers from The Beatles, the Stones and the Kinks, as their stripy surf-band shirts made way for matching sharkskin suits.

  McLaughlin and Swickerath were regular visitors to the Osterbergs’ trailer, in contrast to Jim’s girlfriends, Jannie Densmore and then Lynn Klavitter, who never got to see his home or meet his parents. From Swickerath’s viewpoint, Osterberg had ‘a lonely life. Before school his mom and dad would just sort of shake his foot, say, Jim, get up, and it was up to Jim to get up, get breakfast and get himself to school, as his parents took off for work.’ What was unusual then is of course conventional today. But Osterberg’s upbringing, and only-child status, undeniably contributed to an independent - solitary, even - streak. And a persona that, even in those innocent times, was being noticeably affected by the advent of drugs and rock ’n’ roll. It was towards the end of his time at Ann Arbor High that girlfriend Lynn Klavitter noticed when he ‘started taking overdoses of his asthma medicine. I remember one place we went with the Iguanas, some resort, where he bleached his hair, and I knew something was changing about him. He was doing extravagant things that he normally didn’t do.’

  Over those high school years, Jim’s preferred social setting moved from the golf course to Ann Arbor ’s Discount Records. The store’s manager was Jeep Holland, a well-known svengali on the local scene. He steered blue-eyed soulsters the Rationals to chart success, and built up a thriving booking agency based from a payphone, scaring off other potential users with his scary speed-freak glare. Holland took a liking to young Osterberg, even though the Iguanas were rivals to his own charges. Holland eventually hired him to work in the store after school, checking in and out Discount’s stock of Stax and Volt 45s: ‘But he was always late, never on time. Then I noticed that so many girls were hanging around him that nothing was getting done. So in the end I had him do all the stock work in the basement.’ An expert in soul and R&B, in which he schooled all his charges, Holland enjoyed mocking Jim’s Beatles-loving band - and over that year got into the habit of shouting ‘Iguana Alert!’ whenever Jim emerged from the basement.

  It was during those after-school hours working at Discount that Osterberg first noticed two kids, fellow students at Ann Arbor High, hanging around on Liberty Street outside the store. Ron Asheton was a wannabe rock star with a Brian Jones haircut, who’d first met Jim in the Ann Arbor High school choir; Scott Asheton, Ron’s younger, taller brother, was a charismatic young hood with a dark, glowering air. The pair had moved to Ann Arbor with sister Kathy and their mother, Ann, soon after the death of their father on 31 December 1963. Today, Iggy still recalls Scott Asheton looking ‘magnetic, like a cross between a young Sonny Liston and Elvis Presley’. Many years after their first meeting, he commemorated that first sighting in his song ‘The Dum Dum Boys’, remembering the way ‘they used to stare at the ground’. But over the next few months their conversations would be limited to muttered hellos in the corridors of Ann Arbor High.

  It was with by now typical Osterberg bluster that the lead Iguana described himself as a ‘professional drummer’ in flyers for his unsuccessful presidential campaign of 1965 - his instinct for self aggrandisement had reached new heights. Literally - in that spring’s talent contest he overshadowed his fellow Iguanas by appearing on top of a ludicrous, seven-foot-tall drum riser. (Fellow student and fan, Dale Withers, one of the school’s taller pupils, pondered if this was a classic ‘Napoleon complex’.) But in July 1965, after Osterberg, Swisher and McLaughlin’s graduation from high school, that exalted ‘professional’ claim became true, when the band secured a residency at Harbor Spring’s Club Ponytail, in what several of them would recall as the most idyllic summer of their lives.

  An elegant resort nestling close to Little Traverse Bay on Lake Michigan, Harbor Springs was studded with beautiful, sprawling Victorian mansions that were owned or rented as summer homes by the Midwest’s wealthiest industrial magnates - many of whom had daughters who were keen to party the night away. Recognising the opportunity, local businessman Jim Douglas opened a teenage nightclub at the Club Ponytail, a Victorian mansion that had reputedly once served as a base for Detroit bootleggers during Prohibition. The Iguanas would be the bait for these society debutantes - and before long, it became obvious that Jim Osterberg was their biggest attraction. Located down a two-lane road, and advertised by a huge wooden cut-out of a blonde with a pert turned-up nose and a ponytail, the Club Ponytail’s two dance floors soon became the hottest spot in town.

  For five nights a week, the Iguanas would belt out a set that included several Beatles songs - ‘I Feel Fine’, ‘Eight Days A Week’, ‘Slow Down’ and more - plus the Stones’ ‘Tell Me’, Bo Diddley’s ‘Mona’ and, several times a night, that summer’s smash hit, ‘Satisfaction’, most of the numbers sung by McLaughlin or Kolokithas. By now, Osterberg had decreed that Sam Swisher’s saxophone was superfluous, and the real-estate agent’s son was relegated to bashing on a tambourine (invariably on the on-beat) and looking after the band’s money. According to Sam’s girlfriend, Mim Streiff, Sam compensated for his humiliation by exerting financial control over his bandmates, advancing them money from the next week’s earnings and deducting a lucrative 20 per cent. Naturally this earned the further resentment of his drummer, who glowers at the mention of his name to this day.

  Honed by their two-sets-a-night, five-nights-a-week routine, the Iguanas became a tough little outfit, their voices roughened and funky from constant wear. Cub Koda, later the leader of Brownsville Station, saw the Iguanas many times over that summer, and describes them as ‘a great, greasy little rock ’n’ roll band’. Jim was a good drummer, who’d lie back on the beat and slash away at his ride cymbal, which was studded with rivets for a sleazier sound. ‘And, man, you’d watch those rivets dance,’ says Koda, who was also struck by the Iguanas’ low-down versions of ‘Wild Weekend’ and ‘Louie Louie’; Osterberg would customise them with his own dirty lyrics, which Detroit bands loved trading with each other. Michigan teen band the Fugitives claimed to have introduced the word ‘fuck’ to Richard Berry’s garage-band classic ‘Louie Louie’ back in 1963 but, after dire warnings from Douglas, McLaughlin learned to hover by the microphone’s volume control during the offending song, ready to protect the vulnerable teens of Harbor Springs from lines such as ‘Girl, I’d like to lay you again’, or ‘Her ass is black and her tits are bare’.

  McLaughlin liked and respected Osterberg, but was convinced that such obscenity could never win over an audience. Normally, the drummer got so carried away he didn’t even notice his screamed vocals weren’t audible. Neither did it bother his audience of apprentice teenyboppers, whose ecstatic response encouraged him to try another brief vocal spot, singing the jingle of a then-popular sugar-laden cereal, Sugar Crisp. As their drummer imitated the TV commercial’s wacky cartoon bear singing ‘Can’t get enough of that Sugar Crisp’, Jim’s fellow Iguanas were astonished to see that the resort’s female population had brought boxes of the sugary puffed-wheat concoction to the club, and were throwing it onto the stage as if at some cute performing monkey.

  By the middle of that summer, McLaughlin, Swickerath and Kolokithas noticed that on their weekends off, when they would return to Ann Arbor to see their parents, or girlfriends, Jim invariably remained in their chalet at Harbor Springs, where by now he had been given his own room in a vain effort to stem
the tide of mouldy peanut bars and rotting apple cores that accumulated behind the communal sofa. Much of the time, Osterberg stayed indoors, playing two LPs over and over - Dylan’s Bringing It All Back Home, and The Rolling Stones Now. ‘Not a day went by that I didn’t listen to those things for hours.’ But his bandmates had no knowledge about what else he got up to during his weekends off until, one weekday evening, he invited the others up to an imposing mansion overlooking the bay. Ushered into a large dining room, Swickerath and Kolokithas were astonished to be greeted by a distinguished-looking businessman, who was introduced by Osterberg as ‘Mr Reynolds - he owns the Reynolds Aluminum Company’. The friendly industrial magnate chatted to the assembled Iguanas, telling them what a fan his daughter was of their music, before handing each of them a chisel and asking them to inscribe their names into a huge aluminium table that dominated the room. Soon it transpired that Jim hung out with the daughters of the Wrigley’s Chewing Gum family too, while on other weekends he had worked his charm on Chuck Bowbeer, owner of the Depot House, an arty coffee bar based in a railway carriage, and persuaded him to host Jim’s poetry readings. They never knew whether Jim invited girls other than Lynn Klavitter back to their quarters, but McLaughlin, who at one point had shared a bed with Jim in their tiny chalet, decided to change the arrangement after noticing some fresh stains on the sheets. ‘Sorry about that,’ Osterberg informed him with typical bluster when McLaughlin complained. ‘It was either that or fatherhood.’