Kishore Kumar has several "best" songs, and to make this a bit more challenging and interesting; I shall unilaterally add two constraints:- 1) Solo Songs & 2) One Song Per Hero.
HONK IF YOU KNOW ALL THESE
People may have forgotten these heroes, but the songs Kishore sung for them are unforgettable.
20) Vishaal Anand - Who is he and how did he get such a song, Kishore excels with
Chalte Chalte Mere Yeh Geet Yaad Rakhna, Kabhie Alvida Na Kehna, Kabhie Alvida Na Kehna.
19) Vijay Anand - One of India's best directors, Kishore ensures that we watch him act with
Mera Jeevan Kora Kaagaz Kora Hi Rahe Gayaa, Jo Likha Tha Aansoo'o Ke Sang Beh Gaya.
18) Vinod Mehra - Actually has another good one "Geet Gaata Hoon Main", but Kishore spins magic with **Phir vahi Raat Hai Phir Vahi Raat Hai Khwab Ki, Raat Bhar khwab Main Dekhaa Karenge Tumhe.
*17) Jalal Agha/Rakesh Roshan - Although Rakesh Roshan is the hero, this song was picturized on Jalal Agha. Neither is Hrithik, but Kishore makes us think they are with
*Samaa Hai Suhaana Suhaana, Nashe Mein Jahaan Hai, Kisiko Kisiki Khabar Hi Kahaan Hai, Har Dil Mein Dekho Mohabbat Jawaan Hai.
16) Navin Nischol - I lost a quiz because I did not know the heroine(Archana); play this Kishore song for yours **RaatKali Ek Khwab Mein Aayee Aur Gale Ka Haar Hui, Subah Ko Jab Hum Neend Se Jaage Ankh Tumhi Se Chaar Hui.
15) Anil Dhawan - One of the most under-rated songs about life in Bombay; Kishore Yes!, Bombay Yes! Anil Dhawan?. **Yeh Jeevan Hai, Is Jeewan Ka Yehi Hai Rang Roop, Thode Gham Hai Thodi Khushiyaa, Yehi Hai Yehi Hai Chaaon Dhuup.
*NATIONAL INTEGRATION
Politicians and Cricket Selectors insisted on this category, Kishore possibly had them in mind when he sung some of these.
14) Feroz Khan - Bollywood's Clint Eastwood and the original Khan, Kishore actually manages to make us believe Feroz is a romantic with Tere Chehre Mein Woh Jadoo Hain Bin Dor Kheecha Aata Hoon, Jaana Hota Hai Aur Kahi Teri Oar Chalaa Aata Hoon.
13) Uttam Kumar - Bengali Superstar, fellow Bengali Kishore does not let him down with
Dil Aisa Kisine Mera Toda, Barbaadi Ki Taraf Eisa Moda, Ek Bhale Manush Ko Amanush Banaake Chhoda.
12) Amol Palekar - Marathi Common Man, Kishore's song is far from "common"
*Aanewaala Pal Jaanewaala Hain, Ho Sake To Isme Zindagi Beeta Do, Pal Jo Yeh Jaanewaala Hain.
*11) Sanjeev Kumar - Gujarati Intellectual, Kishore emphasizes his sensitivity with
*Meri Bheegi Bheegi Si Palkon Mein Rahe Gaye Jaise Mere Sapne Bikhar Ke, Jale Man Tera Bhi Kisike Milan Ko Anamika Tu Bhi Tarse.
*To round this category, I would have loved to add KamalHaasan; but I could not find any good Kishore sung songs.
HINDI CINEMA's FIRST FAMILY
Again, Unfortunately I cannot find any good songs(or even any songs) that Kishore sung for either Raj Kapoor or Shammi Kapoor.
10) Randhir Kapoor - Should I choose Kishore's energetic yodeling in "Yeh Jawaani Hai Diwaani"; but RK Films and Raj & Prithviraj Kapoor's presence lead me to select this under-rated evergreen classic Bhawre Ki Goonjan Hai Mera Dil, Kabse Samhale Rakha Hai Dil, Tere Liye, Tere Liye, Tere Liye, Tere Liye.
9) Rishi Kapoor - Similar reasoning to 10, "Om Shanti Om" is the most obvious choice; but the presence of KamalHaasan and Dimple(and above all Kishore) give us **Chehra Hai Ya Chaand Khila Hai Zulf Ghaneri Chaon Hai Kya, Saagar Jaisi Annkhon Waali Yeh To Bataa Tera Naam Hai Kya.
*8) Shashi Kapoor - Which is the best Kishore solo in "Sharmilee"("Khilte Hai Gul Yahaan", "Kaise Kahen Hum Pyar Ne Humko"), we could argue till hell freezes over; in the interests of peace I select
O Meri, O Meri, O Meri Sharmilee, Aao Na Tarsaao Na, Aao Na Tarsaao Na.
JUST MISSED THE TOP
They may have just missed, Kishore certainly did not.
7) Vinod Khanna - Akshay and Rahul must be wishing they too had a Kishore. Narrowly beating another Kishore gem "Ruk Jaana Nahin Tu Kahin Haarke", this one packs an emotional punch.
Koi Hota Jisko Apna Hum Apna Keh Lete Yaaro, Paas Nahi To Door Hi Hota Lekin Koi Mera Apna.
6) Jeetendra - Kishore sings many "Jumping Jack" songs for Jeetu, but the best by far is
Musafir Hoon Yaaro Naa Ghar Hai Naa Thikaana, Mujhe Chalte Jaana Hai Bas Chalte Jaana.
Sunil Dutt deserves to be in this category, he also has some exquisite songs in Padosan("Mere Samnewaali Khidki Mein", "Kehna Hai Kehna Hai"); however I feel that these songs really belong to the actor Kishore.
ECCENTRIC GENIUS
5) Kishore Kumar - Kishore rightly gets a category all to himself; what with "Ek Ladki Bheegi Bhaagi Si", "Mere Mehboob Qayamat Hogi", "Hasrat Hi Rahi Humse Bhi Koi Pyar Karta", "Koi Humdum Na Raha", "Main Hoon Jhoom Jhoom Jhoomroo". He would describe his four wives as "bandariyas", since they were all living in Bandra when he first met them. A man who sings like he does can probably get away with calling anyone almost anything;
Aa Chal Ke Tujhe Main Leke Chaloon Ek Aise Gagan Ke Tale, Jahaan Gham Bhi Na Ho Aansoo Bhi Na Ho Bas Pyar Hi Pyar Pale.
SUPERSTARS
Missing from this category are Dilip Kumar(I just could not bring myself to insert "Saala Main To Sahab Ban Gaya"), and Raj Kapoor & Shammi Kapoor.
4) Dharmendra - Probably the first action superstar, Kishore brought out his gentle side with "Gaadi Bula Rahi Hai", and "Hum Bewafaa Hargiz Na The"; this mesmerizing mellifluous masterpiece is my choice
*Pal Pal Dil Ke Paas Tum Rehti Ho, Jeevan Meethi Pyaas Yeh Kehti Ho.
*3) Amitabh Bachchan - The Angry Young Man, Kishore's singing helped alleviate some of that anger with; "Khaike Paan Banaaraswaala", "Pag Ghoongro Bandh", "Meet Na Mila Re Man Ka", "Tum Bhi Chalo Hum Bhi Chale", "Dekha Na Hai Re Socha Na". A soulful melody gets my nod
Rimjhim Gire Saawan Sulag Sulag Jaye Man, Bheege Aaj Is Mausam Main Lagi Kaisi Yeh Agan.
2) Rajesh Khanna - Arguably the Kishore-Rajesh combination could account for a majority of Kishore's best songs. Kishore's singing was a major factor in Rajesh's romantic image, with songs such as "Mere Sapno Ki Rani", "Pyar Deewana Hota Hai", "Chingari Koi Bhadke", "Zindagi Ek Safar Hai Suhaana", "Mere Naina Saawan Bhaadon", "Meri Pyaari Beheniyaa Banegi Dulhaniyaa"; I shall select the sensuous from Aradhana
*Roop Tera Mastaana Pyar Mera Deewaana, Bhool Koi Humse Naa Ho Jaaye.
*1) Dev Anand - "Marne Ki Duayen Kyon Maangu", Kishore's first song was picturized On Dev Anand(1948 Ziddi). Kishore-Dev have generated megahits in the 50's("Hum Hain Raahi Pyar Ke", "Maana Janab Ne Pukara Nahin", "Dukhi Man Mere"), and the 60's("Khwab Ho Tu Tum Ya Koi Haqueeqat", "Yeh Dil Na Hota Bechaara") and the 70's("Phoolon Ke Rang Se", "Phoolon Ka Taaron Ka", "Pal Bhar Ke Liye Koi Hame Pyar Kar Le"). After Kishore's death in the 80's, Dev Anand may have lost his bearings; he and us should remember this 50's Binaca GeetMala Sartaj Classic
Jeevan Ke Safar Mein Raahi Milte Hain Bichad Jaane Ko, Aur De Jaate Hai Yaaden Tanhai Mein Tadpaane Ko.