The on-screen chemistry of Cybill Shepherd and Robert Downey, Jr. reflected an off-screen rapport that developed as Shepherd helped Downey ease into his role. Downey said, "Cybill helped me to take my time at what I was doing. She taught me that I didn't have to be talking every minute, 'It's alright if you just look at me for five seconds and don't say anything', she'd say."
The inspiration for the movie came to Screenwriters Perry Howze and Randy Howze, who are real-life sisters, from a true story their grandmother told them about their great-aunt. "Our aunt", related Perry, "was married to the love of her life, a southern stock broker, for one year. They were a young, beautiful, glamorous couple. After a year of bliss, he died of a brain tumor, and our aunt never recovered. She was that committed and devoted to him." Randy continued: "We thought, wouldn't it be a joyous thing if her husband came back into her life. We like that notion of life and love not ending with death, just continuing and changing form."
To add further realism to Corinne Jeffries' (Cybill Shepherd's) fund-raising gala for the exhibit, the filmmakers enlisted America's foremost band-leader, Lester Lanin, to preside over the dance orchestra. Lanin, who had played nine out of the last ten Presidential Inaugural balls as well as at the wedding receptions for Prince Charles and Princess Diana; and Prince Andrew and Sarah Ferguson (a.k.a. Princess Sarah), was delighted to participate in the film.
Once Cybill Shepherd was secured, the filmmakers then faced the formidable task of casting a young actor to star opposite her, as her "recycled" husband. The part required an accomplished performer who could portray a multi-dimensional role, an appealing leading man who could balance romance with comedy, as well as convincingly playing two characters in one. Robert Downey, Jr., named the "Hottest Actor of the Year" by Rolling Stone Magazine, was their man. A veteran film actor, Downey's memorable performances in a variety of roles, both supporting and starring, had earned him critical respect and audience popularity. Emile Ardolino said, "Robert is an extraordinary talent, who is skillful, passionate, innately funny, sexy, and always surprising. He brings a tremendous amount of vitality and complexity to all of his performances.
Attention to detail for the look and feel of the film extended to Cybill Shepherd. The filmmakers and Shepherd wanted her character of Corinne Jeffries to appear as different as possible from her Moonlighting (1985) Maddie Hayes character. To achieve this, they cut her hair at least five inches in a more conservative style. Costume Designer Albert Wolsky draped Shepherd in a lot of black and/or structured clothing at the beginning of the film, also noting that "We never see her wearing black on Moonlighting (1985)." In the second half of the film, as Corinne Jeffries (Cybill Shepherd) starts to mentally and physically open up, Wolsky dressed her in softer, more voluminous creations. Wolsky explained: "Her colors get softer, the fabrics go from wools to chiffons and cottons." Director of Photography William A. Fraker highlighted Shepherd with his own special brand of luminous lighting. The veteran Cinematographer was well suited for the movie, not only was his work highly respected within the film industry, but, having shot Shepherd in her Loreal commercials, Fraker was very familiar with the actress.
Heart and Souls (1993) is another romantic comedy fantasy starring Robert Downey, Jr. about misplaced souls, though this time the souls are stuck with him after a traffic accident at the time of his birth.
The film opens up in Washington, D.C., in the 1960s. The setting was deliberate. Randy Howze explained: "Washington was magical then. The Kennedy Presidency was in full force. There was so much promise, and like that, Corinne's life starts out so blissfully. She is marrying the man of her dreams, Louie Jeffries. The couple has everything going for them, and ahead of them, like the 'Camelot Years', and then, boom, it all ends, and we cut to twenty years later, where again the times are reflected in Corinne's life. She's now a modern working woman, and a single parent."
Real-life Washington Post journalist Benjamin C. Bradlee wasn't the only genuine Washington, D.C. article to appear in the movie. Ben Bradlee, in the film, is a real-life character based on Benjamin C. Bradlee, and is played in the movie by Henderson Forsythe. Perry Howze said: "We sent him (Bradlee) the script, and he and his wife Sally Quinn read it, and loved it. His only stipulation was to clean up his language. We had a few 'hells' and some choice expletives coming out of his mouth, and he said, 'for God's sake, get those four letter words out. I don't talk like that'." The real-life Bradlee later appeared in the documentary Fuck (2005).
Perry Howze and Randy Howze brought their script to Producer Mike Lobell, who immediately responded. Lobell said: "I loved the story, and the people at TriStar felt the same way. The story moved everyone because it's about people, love, memory, and it's also very funny."
Mary Stuart Masterson noted of her character Miranda, that it added a new dimension to her repertoire: "Miranda is more intellectual than any other character I've played, You know, I usually play street smart urchins, pregnant, and barefoot." Nonetheless, the press kit states Masterson personally related to Miranda: "I went to schools very much like Yale. They were pressure cookers." she said of her years at the prestigious Dalton School in New York City, and later at New York University, where she studied anthropology and film."
Determined to present as realistic a setting as possible, Perry Howze and Randy Howze decided to employ Corinne Jeffries (Cybill Shepherd) as the curator of the Smithsonian Institute's U.S. President First Ladies' Gowns Exhibit, a show that had dazzled them when they had visited it as children. Corinne Jeffries' predicament, as invented by the Howzes, is to raise funds to enlarge the First Ladies display, through a gala event. They queried the Smithsonian, asking if this character and her plight sounded plausible. It was more than plausible. The Smithsonian, in fact, was trying to raise two million dollars for the display. Their first Ladies' Gowns Exhibit, once an extravagant show, had been reduced to one alcove, with the rest of the exhibit in storage.
The film was described by Emile Ardolino as "A romantic comedy about love, and the transforming effect it has on our characters' lives. It's about people who learn to live mortally in the present by letting go of the past. Imagine this happened to you: you're a normal person, and all of a sudden you get your memory back from your past life, and you realize that your girlfriend is your daughter, and her mother is your wife from your previous life. I was intrigued by the comic possibilities of this predicament. We've all probably gone to a place we've never been, and felt like we've been there before. We've met a person for the first time, and felt as though we've known them our entire lives."
Cybill Shepherd was the first choice of Mike Lobell and Director Emile Ardolino to play Corinne Jeffries. Lobell noted, "When I read the script, I thought that if Cybill was going to return to features, this should be it, because the film is a romantic comedy, and I always thought of Cybill as very funny in a Carole Lombard way." Ardolino noted that Shepherd shared qualities with her character that made her the ideal candidate for Corinne Jeffries. Ardolino said, "Corinne is beautiful and determined, yet she's vulnerable, with a sense of humor, not unlike Cybill's own. Corinne is loyal and passionate and obsessed with love, because she cares so deeply about someone."
The picture was shot in the U.S. on-location in Washington, D.C., and featured some of the city's famous landmarks, including Capitol Hill, the Smithsonian Institute, the Washington Post, the Jefferson Memorial, and the historic city of Georgetown.
The movie appealed to Cybill Shepherd for two reasons, which were her character Corinne Jeffries, and Emile Ardolino. Shepherd said, "When I found out Emile Ardolino was going to direct it, I knew it was going to be a tasteful project, because of Dirty Dancing (1987), his outstanding work on PBS, and his Academy Award-winning documentary He Makes Me Feel Like Dancin' (1983)." Corinne Jeffries interested Shepherd because she was a departure from her real persona, and from her television alter-ego of Maddie Hayes on Moonlighting (1985). Shepherd noted: "Many moons ago, Stella Adler told me I should play what I haven't lived. It would help me with life, and so I've used this as a general guide for parts. Corinne was a good part for me, because it offered a lot of challenges. To play a character at twenty-one, and again in her early 40s. Someone who experiences the devastation of losing her husband, and a mom with a grown up daughter. All those things, except being twenty-one, which I have no interest in being again, were new to me."
Show-business trade-paper "Variety" said of this movie in its review, "Here comes Chances Are, and there goes Mr. Jordan", a reference to the earlier heavenly comedy Here Comes Mr. Jordan (1941), which had been remade as Heaven Can Wait (1978).
Snaring two Washington, D.C. prime locations, the Smithsonian Institute and the Washington Post, proved to be challenges indeed. As Mike Lobell explained: "The Smithsonian took about four months to give us the go ahead. They, for good reason, were very concerned about how they would be portrayed to the public. We had to assure them that we would present the institution in the best possible light. They finally agreed, and treated us wonderfully in Washington." Securing the Washington Post was due, in part, to Perry Howze and Randy Howze. Lobell said, "We were fortunate because our screenwriters, who grew up in Washington, D.C., had been childhood friends of Benjamin C. Bradlee's daughters, and therefore knew Bradlee." The production got the full support of the Washington Post, filming in front of the building, inside the press room, in its lobby, and at its printing presses. This was quite a coup it was thought by the filmmakers, considering that the newspaper had refused to cooperate with the filming of All the President's Men (1976).
The filmmakers immediately thought of Mary Stuart Masterson to play Corinne Jeffries' (Cybill Shepherd's) daughter Miranda, the independent Yale law student powerfully attracted to her Yale classmate-turned-house-guest, Alex Finch (Robert Downey, Jr.). When approached for the role, Masterson was initially noncommittal. Mike Lobell's tenacity, however, was persuasive. Masterton recalled: "I went to Sundance, Utah, to think things over and ski, when Mike Lobell came skiing down the slopes after me with pen and contract in hand, saying, 'you must do this movie, it will be the best thing you've ever done'. He was obviously very convincing."
The amount of time between husband Louie Jeffries (Christopher McDonald) passing away in 1964, and then returning as another person inside Alex Finch's (Robert Downey, Jr.'s) body in 1987, was twenty-three years.
Ryan O'Neal was cast as Philip Train. Perry Howze and Randy Howze described Philip Train as "a noble character, the last gentleman roaming the earth, because he has respected Corinne Jeffries (Cybill Shepherd) and her love for her late husband, who was also his best friend, so much, that he has never tried to impose himself on her. He doesn't want to jeopardize their friendship. This kind of character doesn't exist in 1988, but we want him back in the world." The film's press kit states: "(Ryan) O'Neal endowed Philip (Train) with the strength, vulnerability, and comedic sensitivity needed to ennoble this endearing underdog, a character who gives true modern meaning to the word 'gentleman', as he waits for the woman he quietly loves, to someday take serious notice of him."
After viewing Dirty Dancing (1987), Mike Lobell was certain that Emile Ardolino had the proper sentiment, compassion, and intimacy to direct this film. Lobell explained, "I could see that Dirty Dancing (1987) was directed by a man who had a lot of heart, which was exactly what I wanted for our film."
Emile Ardolino and William A. Fraker wanted to give the movie a cohesive look, that would convey an old-fashioned romantic comedy, but they also wanted to emphasize certain distinctive aspects of the film. For example, the scenes set in the early 1960s would have a unique ambiance, distinguished from the scenes set in the present, and those set in a heavenly place, which the filmmakers refer to as "Limbodrome", had to be unusual and ethereal.
The accident scene that concludes the 1964 section of the story, was filmed on the night of June 7-8, 1988, when the TriStar film crew secured permission from the Mayor's Office of Film and TV Development, District of Columbia, to close Wisconsin Avenue NW in Georgetown between M and O Streets NW between 4 p.m. on Tuesday until dawn on Wednesday. Around two dozen 1960s vintage automobiles were secured from area car club members, many driven by their owners, to dress the street. These included a 1956 Buick Century, a 1957 Ford Fairlane 500, a 1959 Cadillac Seville, a 1959 Chevrolet Biscayne, a 1960 Mercury Comet dressed as City Cab 101, a 1960 Pontiac Star Chief, a 1958-1960 Edsel, a 1962 Studebaker Lark, a 1963 Chevrolet Corvette, and a matched pair of 1964 Volkswagen Beetles. The "Bug" is driven in the film by Louis Jeffries, and he is struck crossing Wisconsin Avenue by the Studebaker.
Uncredited anywhere is the thriller REINCARNATION OF PETER PROUD (1975) which has a similar plot line - a man seeking the truth about his flashes of memory discovers he must have been reincarnated after a violent death. While visiting his old home, he falls in love with (unknowingly) his own daughter, which his original wife will seek to prevent. Surely more than coincidence that CHANCES ARE utilized this, unless a film can itself be reincarnated.