Imagine you’re an insecure, unimposing male freshman at a school dominated by forthright, often angry women. Overwhelmed by your regular academic schedule, by the often humorless discourse in your psychology class (in which you are the only male student), you enroll in a film studies course, where you hope your goofy pluck will endear you to classmates. Instead, you are ridiculed, on the very first day, by professor and students alike, for not “grasping” the professor’s monstrously pretentious, self-satisfied art film that he presents to the class. The infamy only grows when you broadcast your own films–lighthearted spoofs of comic-book fantasies, quirky profiles of eccentric students–which lack the “artistic drive” your sycophantic classmates bring to their own films. You are dismissed as a fool by the aesthetes, but you’re not outgoing enough to fit in with the pretty ladies on campus, so life is pretty lonely.

Cut to several years later. A hot director comes to school and allows your current film class to co-write and act in a heavily improvised project–a film that later attracts Kirk Douglas and Vincent Gardenia. For reasons unknown, you are selected to be the casting director. After this life-changing experience, the director still takes a shine to you, so you bring the rough cut and script of your original, mostly autobiographical film, “The First Time,” to him, for advice. He brings up your funny, bittersweet tale of freshman year film class and coed-related woes that you have regaled him with, suggests that you make that the comic centerpiece of your debut film. You oblige. He becomes your creative consultant and executive producer.

“The First Time” gets made for a paltry $250,000, half of it raised by family members, half by a fledgling new studio called New Line Cinema. Wallace Shawn gets cast in the juicy role of your former, pompous professor. The movie’s release is badly marketed, at first, and all hope is lost…but then a saintly publicist gets three top critics to attend a screening. One of them raves about the film. Other reputable publications cover its re-release. The audience reaction is highly positive. At 22 years old, you have pulled off one of the most unexpectedly triumphant independent film debuts in cinema history. Things can only go downhill, from here. And–not tumultuously, but still surprisingly–they do…

This happened to Riverdale-bred filmmaker Charlie Loventhal between the late 1970s and 1983. The school was Sarah Lawrence College. The hot director was Brian DePalma, who visited the school, with “Carrie” and “The Fury” under his belt, in 1980, to recruit students for a ragtag, hastily shot, intermittently funny dark comedy called “Home Movies.”

The film marked the first starring role for Keith Gordon, and also featured Nancy Allen. Loventhal selected Gordon, Allen and other actors from thousands of hungry try-outs at DePalma’s Greenwich Village office.

“A lot of people were upset that I looked about 16 or 17—I was 20—and I was the guy who had to get through to meet Brian DePalma,” said Loventhal, who speaks in a lilting voice resembling Kermit the Frog at his most earnest. “I remember Ellen Barkin came in. She didn’t have an agent. She was one of the finalists.”

“Home Movies” concerns lovesick teenager Gordon’s flailing attempts to lure alcoholic sex kitten Allen away from his brother/her fiance (Gerrit Graham). The brother, a Boy Scouts instructor, is an abusive control freak who behaves repressively towards Allen but secretly teaches the scouts how to copulate (Loventhal played one of the spooked scouts). Meanwhile, Graham and Gordon’s father (Gardenia) is having an affair, and camera enthusiast Gordon tries to document it. In a promising framing device that never quite pays off, a filmmaker/teacher (Douglas) tells his class that he is documenting Gordon’s life on camera; therefore, everything we see happening to Gordon is technically part of Douglas’ film. But Douglas pretty much disappears from “Home Movies” after the first scene, so we’re left with Graham’s hysterical acting, Gordon’s earnestness and a more strange than funny subplot about Allen’s split personality alter ego, a profane stuffed rabbit. All of this is underscored by cheap-sounding synth music usually relegated to porn films.

Still, the film has its zany moments and it put Loventhal on the map; had he never met DePalma, we’d surely have never seen “The First Time.” It is a wonderful film, with humor that ranges from pitch-perfect wry (anyone who’s ever sat in on a liberal arts college class will laugh and wince in recognition at the film course scenes) to innocuously vulgar (a lusty fat girl sneaks into the protagonist’s dorm bed; a guidance counselor obsesses over the hero’s sex life more than his grades). And some of the touches are no doubt stolen from Woody Allen (ie, the hero’s nagging Jewish mother barges in on him at school) but dressed up with contemporary twists (she does so by disguising as a hip 50 year-old film student). It is an absolute must-see, and Loventhal has not given up trying to get the film out on DVD.

Long before “The First Time” ever saw the light of day, Loventhal had proven his talent with an impressive repertoire of home-made and school assignment comedies. His parents gave him a Super 8 video camera when he was 10, and his style was soon influenced by early Woody Allen films (“Sleeper,” “Take the Money and Run”) and Preston Sturges (he later named his film company, Presto Productions, after the celebrated director). His premiere student film was called “Seduction of Superman.”

“The criminals can’t do any crime because of Superman, and [they discover] that Superman has an untapped sexual reservoir,” Loventhal explained. “He’s a virgin, and if he was aware of his sexuality, he’d just want to have sex and not fight crime anymore. The last scene of the movie is Superman whistling for women at Times Square, while crime is rampant in Metropolis.”

This, and later works such as “Al Jones Talks to Women”–a cinematic document of a boastful, older student’s failed attempts to seduce coeds–did not resonate with Loventhal’s classmates, a disconnection captured to hilarious effect in “The First Time.”

“I was making stuff like ‘Al Jones’ and they were making important things, like a woman scrubbing the floor for 20 minutes,” Loventhal remembered. “The first day, the professor showed his film, of a ceramic hand on a record player, going round and round for 20 minutes. I didn’t have a clue what it was about, and when the lights came on, everybody else in the class loved it. They said ‘Wow, how did you get the light to gleam off the fingernails?’ Everyone but me tried to follow his lead. They just hated my stuff. This guy screamed at me, ‘Why are you wasting our time?!'” (An eyepatch and beret-wearing Robert Trebor gives a masterful performance in “The First Time” as this infuriated youth).

While casting “The First Time,” Loventhal, on the hunt for “odd-looking” people, hired Larry “Bud” Melman (real name Calvert Grant DeForest) to play a film festival judge, shortly before he became a cult figure on Late Night with David Letterman.

“A year after the movie wrapped, he came on Letterman as a guest and showed a clip from the movie. He was my good luck charm, so I tried to put him in everything,” said Loventhal. “In ‘My Demon Lover,’ he’s the guy at the health food restaurant that chokes to death. We finally gave him lines for ‘Mr. Write.’ We had to give him cue cards. He was really nervous. He was the sweetest guy.” [Sadly, like Melman, Loventhal’s friends/”First Time” co-stars Tim Choate and Wendie Jo Sperber died, respectively, in 2004 from a motorcycle accident and 2005 from breast cancer.]

Also considered for “The First Time” was Ellen Barkin, again, for the part of the mean-spirited dream girl, and Dana Delany.

New Line marketed “The First Time” in 1982 as “a tits-and-ass film, but it wasn’t. They opened it at these drive-ins in the south, and people hated it, so it was basically dead. My career probably would have ended at 22, but I found a publicist who arranged a screening for Pauline Kael, David Ansen and David Denby. If it wasn’t for Denby, I’d probably be a pizza guy right now. He loved the film. I think his wife had gone to Sarah Lawrence. Pauline thought it was OK, and Ansen liked it, but Denby championed it.”

“In the past, I’ve deplored this kind of getting-laid-at-Sarah-Lawrence movie, but ‘The First Time’ transcends its type,” Denby raved in his July 18, 1983 New York Magazine review. “Some of the gags are frighteningly juvenile, but Loventhal has a true entertainer’s instinct.” (The phrase “frighteningly juvenile” could certainly describe large parts of Loventhal’s next–and last–three directorial efforts, but for me, even his lesser films are suffused with so much good-natured zeal that it’s hard for me to dislike them. That’s why I referred to Loventhal’s films as silly in a “critic-proof” way. Big-time critics, as you will soon see, weren’t so charitable later on.)

Later that month, the New York Times’ Vincent Canby followed suit with his own glowing review as well as a Sunday Times profile of the film; “His message…is that art is all very well in its place but movies that make people laugh are far more precious….Mr. Loventhal should have no trouble entering the mainstream of American movie production,” Canby wrote in the latter piece. This would prove to be a no-doubt flattering but somewhat presumptuous projection on Canby’s part.

Thanks to the assistance of independent film entrepreneur Michael Barker (now co-president of Sony Pictures Classics), “The First Time” received a well-attended opening at New York City’s Embassy 72nd Street Twin Cinema. “There was a Woody Allen festival on one side [of the theater] and my film on the other. There was a line around the block, and I thought it was for Woody Allen, but it was for my film. I think we ran six or seven weeks, which is an impressive run if you have very little money.”

Unfortunately, the golden period was short-lived. “The First Time” was released when the video market was still quite undeveloped, and though it received a decent cable TV showing, it has still failed, to this day, to reach a widespread audience.

“The rights were co-owned by my brother and New Line, and then I think all the rights reverted back to us. But it was a complete mess,” Loventhal groaned. “I think the negative—it’s gonna make me sad to think about it—but I have to figure out what we even have to get a DVD made. It was shot on Super 16mm and they did a blow-up, but I think that’s long gone.”

Indeed, distribution of “The First Time” is spotty at best. The copy of the VHS version I purchased was copyrighted in 1996 and has three actors not from the original movie on the front cover.

. At least my version has the correct title; Loventhal said that a few unauthorized copies (that have since been pulled) were marketed as “Doin’ It.”

Slightly easier to find–as it remains a cult favorite–but not available on Netflix or on DVD, is Loventhal’s second directorial effort, “My Demon Lover” (he did not write the script), which was assigned to him by New Line.

That schlocky rubber outfit above gives you a sense of how low-budget and tacky “My Demon Lover” looks (though according to Loventhal, the budget was over $4 million, New Line’s largest allowance at the time). It was clearly not as personal a project to Loventhal as “The First Time,” but, coming after a three-year dry spell of countless development deals that never came to fruition, he was happy to get back to work.

“The first person we made an offer to for the lead was Jay Leno,” he said. “He passed. I had seen him on Letterman and he had a great face, and I thought he’d be good at playing someone possessed. Meg Ryan accepted the [lead female] part, but a week later she was offered ‘Innerspace.’ But she’s still a good friend of mine. We’re developing something together now.”

Not even the oddball appeal of matching Leno with Ryan could have made “My Demon Lover” an out-and-out winner, though they may have charmed audiences more than the hairy, throaty, desperate-to-please Scott Valentine (of “Family Ties” fame) and the so-quirky-it-hurts performance from Michele Little. The jokes are sitcom-style bland (says Little’s sultry, Hispanic best friend to a nerdy teacher who’s hitting on them: “You wanna score, score your term papers!”) The special effects, which Loventhal admits gave him difficulty, consist mostly of exploding yellow paint and monster wings, horns and snouts that appear to be constructed from papier-mâché. Whenever Valentine morphs–because of a Gypsy curse, he becomes a demon when rendered horny–it is usually off-camera. You can see strings when the good demon and bad demon engage in airborne battle at the film’s climax.

But that said, some of “Lover’s” visual design is impressively gritty. The New York street scenes are shot in wide angle so you see the whole of the realistic-looking extras, the graffiti-lined streets and cramped stoops of the then-seedy East Village. And the finale is one of the few cinematic scenes actually shot in Central Park.

“My Demon Lover” is a letdown after “The First Time,” but it certainly didn’t deserve its scathing reviews, upon its theatrical release in April 1987. “Loventhal’s frenetic direction would barely suit a sitcom, let alone a film that also sets out to scare,” Janet Maslin wrote in the New York Times review.

“It was pretty painful to read what a loser you are,” said Loventhal. “My parents went to the New York Times building the night before. We’d had such a great response on ‘The First Time.’ All I really knew was great reviews, and the Times hated it. My biggest memory was that they tested the film before it opened and the marketing people told me it would open at five or six million. And I think the magic number was $2.8 million. And life was not too good.” (There was one happy outcome, though: Loventhal and Valentine are still friends and occasional business partners–they co-produced the 2002 crime film “Deuces Wild.”)

After directing a few one-act plays in New York, Loventhal and his brother Leonard established Presto Productions and took on a few clients. Among the clients were a pair of struggling playwrights, whom the Loventhals hired to adapt a book. Those playwrights were David Crane and Marta Kauffman, later the co-creators of “Friends.”

In 1990, Loventhal relocated to Los Angeles–where he has remained ever since–to develop “Mr. Write,” a Paul Reiser comedy that wound up wrapping in 1992 but was not released theatrically–and only in LA, at that–until the spring of 1994.

“I think it was one of the happiest group of people ever,” Loventhal recalled. “The producers were really smart. I had more experience, and for most of the shoot I had two amazing DPs. Elliot Davis [“Out of Sight”], and then the last week he had to leave, so we got the guy who shot “Pretty Woman” [Charles Minsky]. I’d never worked with people of that caliber. I put some soap opera stars in it, because I’d worked with a few in my plays back in New York, and I’d learned about the fanaticism of soap fans, so I thought it’d be a great marketing tool. And it turned out not to be.”

The movie proved to be a bit broad for critics; the Los Angeles Times’ Kevin Thomas called it “sub-Woody Allen material.” However, as with me, Loventhal’s gently irreverent spirit proved to be infectious; Thomas added, “Loventhal’s direction is so clearly committed, so determinedly energetic, that at least [the cast] is able to make favorable impressions.” It is just pretty damn hard to outright trash Charlie Loventhal.

Not that he wasn’t stung by the mostly negative response. “Martin Mull and I went out to dinner after the premiere, and he said he had a really good time shooting it,” he reflected. “The next day, I read some review and it said that I wasted the talents of Martin Mull. You just want to tear your hair out.”

“Mr. Write” is about a frazzled playwright (Reiser, in frazzled mode) who gets hired to write an inane ad for Ding-a-Lings (a fill-in for Ding-Dongs). He woos the ad’s director (Jessica Tuck), debates whether or not to sign a contract with her slimy ad exec father (Mull) and dodges Tuck’s crazed, touchy-feely boyfriend (Doug Davidson).

As with “Demon Lover,” the jokes (again not written by Loventhal) in “Mr. Write” are often painfully obvious; says Mull, asking Reiser to write an advertisement script for his new product Blue Balls, “I want to put my Blue Balls in your capable hands.” The music is all saxophone muzaq, straight-to-TV slick. But there’s some delightfully inconsequential humor here. On Reiser and Tuck’s first date, she passes out drunk and has a dream that she slept with him; she later thinks they actually slept together. Reiser woos her–for reasons I still don’t get–in a life-sized polar bear suit. He gets caught–while breaking into her room–on an elastic antenna cord. It’s fun to watch Thomas Wilson (AKA Biff from “Back to the Future”) play an insecure ladies’ man decked out in a Hawaiian shirt. And Davidson is hysterical as the boyfriend, as is Melman as an irate drama coach.

Little was heard from Loventhal during the latter half of the 1990s. Several projects came and went, including one starring the apparel fashion twins Chip and Pepper Foster. “The independent market had changed. If you don’t get offers from one of the top distributors, you fall into a big vat,” he said.

Early in the 2000s, Loventhal and Valentine teamed up to co-produce and co-finance “Deuces Wild.” The film was originally executive-produced by Martin Scorcese, but he chose to remain uncredited; as it stands, the film, released in 2002, is a flashy, comically derivative mash-up of “A Bronx Tale,” “Mean Streets,” “Goodfellas” and virtually every other New York City gangster film with a doo-wop soundtrack. Naturally, the backstage drama associated with “Deuces Wild” is more interesting than the film itself; Loventhal was wary about disclosing too many details, but the little he revealed was awful juicy.

“The original cast was Freddie Prinze, Jr., when he was literally the hottest kid in town, right after ‘She’s All That,’ and Josh Hartnett. Reese Witherspoon and Brittany Murphy were interested. Basically, this producer–who I don’t want to speak too ill of because he’s not alive anymore–came to Scott Valentine and me with the idea. We found the money. There was a German financier [Willi Bär] that Scott and I knew, that wound up co-financing. There was a cool guy at MGM. We brought the parties together. And then we couldn’t even get on the set of our own film!”

“The producer kind of chased everybody out of the deal. And then we brought on another producer, and the two of them double teamed everybody. Freddie was willing to work for ten percent of his quote. He was totally excited about it, he was gonna be a producer on it, too. And unfortunately, this other producer made it not much fun for him. Right when Freddie left, the picture fell apart. The cast we got was not quite at the same level. We still got some excellent people, because all the young actors wanted to work with [director] Scott Kalvert [“The Basketball Diaries.”] But there was such an in-fighting war behind the scenes.”

“One of the [two difficult producers] used to be my friend. I’ve seen articles on him, and they asked him, ‘How did you get $10 million for ‘Deuces Wild?’ And everything he said was a lie. It’s a weird feeling when you see someone bald-face lying and no one even checks his story.”

Undeterred by the aftermath of “Deuces Wild,” Loventhal wrote and directed his last movie to date, “Meet Market,” in 2003. It played at a few festivals, met with little fanfare and disappeared, but in 2008, its star/co-producer Julian McMahon (by then well-known for his role on “Nip/Tuck”) helped orchestrate a DVD release. (The film is designated as “Saved,” AKA “in limbo,” on Netflix). McMahon plays a vacant stud/oversensitive actor who’s fought over by two very different women: the prissy Aisha Tyler and the alternately lusty and venom-tongued Krista Allen. (There’s a neat cross-cutting sex scene involving these three). Other subplots: Alan Tudyk can’t meet a nice, normal girl; one is so sexually overzealous that he’s forced to whack her in the head with a dildo. (That fixation continues: in another scene, Allen mistakes a dildo for a ringing telephone.) Elizabeth Berkley is an aspiring actress tired of being hit on by agents, bar-goers and other horndogs; after a fat pizza chef inquires, “May I taste you?” she is driven to murdering any offenders. In the film’s only poignant subplot, a beautiful lawyer has an experimental fling with a dread-locked, drugged-out lesbian. The common thread between these stories (most of which are lifted from Loventhal’s one-act plays) is that several of the characters meet at the local supermarket, while other characters just have missed connections there.

The film is a bit disorganized; some of the acting is hysterically over the top, and some of the jokes are groan-worthy double entendres. Still, Loventhal’s patented sympathy for down-on-their-luck men, his zeal for farce, almost negates any structural weaknesses. “Meet Market” isn’t really a film you can hate because everyone in it is having so much fun, and it’s impressive that Loventhal pulled off a name cast with such a tiny budget. He even manages a few clever porn title inventions: “Scrotal Recall,” “Schindler’s Fist,” “Terms of Enrearment.”‘

“It was a great experience creatively but not as good business-wise,” said Loventhal. “There’s not a lot of good buyers out there and the video market isn’t what it used to be. It hasn’t even played on television, which is surprising, with this cast.”

Still, Loventhal is not down for the count yet. He’s working on an adaptation of the 1953 Jim Thompson novel “Recoil,” adapted by his pal Ralph Pezzullo; James Foley is slated to direct, and a financier is supposed to make a deal this year. He also co-produced–along with McMahon–a Franklin Martin-directed documentary called “Long Shot; The Kevin Laue Story,” about the only one-armed Division I college basketball player. He hopes it will premiere at the Los Angeles Film Festival this year; he’s also working on a feature film version, also directed by Martin. He and McMahon are developing a film adaptation of “Bob’s Office Holiday Party,” a cult LA theater favorite. And he’s still got that work in progress with Meg Ryan (with director Andy Fickman on board).

He bears no grudges about his various hardships, no noticeable bitterness, though he’s clearly not naive anymore.

“There’s certainly a brutal side to the business that I learned about early. When ‘The First Time’ came out, people called me a comic genius. There was a big studio executive—I won’t say who—who said that to me, and then less than two years later, I bumped into him at a party and he had no clue who I was.”

“You can lose your spirit,” Loventhal added in that gentle Kermit voice, “but I’ve tried to stay the course and treat everyone really well. I’m grateful to Bob Shaye [founder of New Line] for giving me a chance. I love what I do and am working with amazing people, and while the journey has been far from smooth…..I like my life and my chances.”