| Cover | | Date
 | Title  Album | Points
 | US peak | UK peak | US AC peak | US R&B peak | Comment |
|---|
| 1. | 10/1978 | | 114
 | 9 US | | 10 AC | 6 R&B | [songwriter #3 hit] [Clouds 11] written by Bobby Caldwell & Alfons Kettner |
| 2. | 05/1979 | | 5
 | 103 US | | | 36 R&B | [Clouds 15] written by Bobby Caldwell  |
| 3. | 09/1979 | | 2
 | | | | 40 R&B | [Clouds 18] written by Bobby Caldwell  |
|
| 4. | 02/1980 | | 7
 | | | | 16 R&B | [Capitol 4826] written by Alfons Kettner & Bobby Caldwell  |
| 5. | 03/1980 | | 1
 | | | | 73 R&B | [Polydor 2066] written by Bobby Caldwell & Alfons Kettner |
| 6. | 04/1980 | | 19
 | 42 US | | | 28 R&B | [Clouds 21] written by Bobby Caldwell  |
| 7. | 03/1982 | | 5
 | 105 US | | | 54 R&B | [Polydor 2202] written by Bobby Caldwell  |
| 8. | 09/1982 | | 9
 | 77 US | | | 67 R&B | [Polydor 2212] written by Bobby Caldwell  |
| 9. | 08/1985 | | 18
 | 87 US | 90 UK | 8 AC | 65 R&B | [Motown 1802] written by Bobby Caldwell , Franne Golde & Paul Fox |
| 10. | 09/1986 | | 162
 | ✫1 US | 78 UK | ✫1 AC | | [songwriter #1 hit] [Full Moon 28597] written by Bobby Caldwell & Paul Gordon |
| 11. | 07/1987 | | 4
 | 91 US | | | | produced by David Foster written by Steve Kipner, Bobby Caldwell & Bill Champlin |
| 12. | 1988 | | 2
 | | | | 42 R&B | written by Bobby Caldwell & Dennis Matkosky |
 | 13. | 12/1989 | | 129
 | 5 US | | 2 AC | | [songwriter #2 hit] written by Jason Scheff, Chas Sandford & Bobby Caldwell  |
| 14. | 1991 | | 2
 | | | 41 AC | | [album cut] written by Bobby Caldwell & George Jimmy |
| 15. | 01/1993 | | 76
 | 55 US | 15 UK | 3 AC | | [songwriter #5 hit] [EMI 50428] written by Bobby Caldwell & Alfons Kettner |
| 16. | 01/1993 | | 1
 | | | | 88 R&B | [Sin-Drome 1174] written by Bobby Caldwell , Franne Golde & Paul Fox |
| 17. | 11/1995 | | 42
 | 102 US | 20 UK | | 51 R&B | featuring Teddy [Noo Trybe 38517] written by Bobby Caldwell , E.A. Ski, Jerold Ellis, Garrick Husbands, Alfons Kettner & Mark Oglelton |
| 18. | 1996 | | 2
 | | | | 42 R&B | written by Darryl McClary, Janai Abercrombie, Michael Allen, Paula Pierre-Louis, Traci Nash, Ali Shaheed Muhammad (sample), Q-Tip (as Jonathan Davis) (sample), Malik Taylor (sample), Bobby Caldwell (sample) & Alfons Kettner (sample) |
| 19. | 12/1997 | | 29
 | 60 US | 35 UK | | 34 R&B | featuring 112 written by Bobby Caldwell , Hubert Eaves III, Clark Kent, The Notorious B.I.G. & J. Williams |
| 20. | 01/1999 | | 108
 | | 3 UK | | 68 R&B | [songwriter #4 hit] featuring Will Smith [MJJ Music album cut] written by Robert Bell, Ronald Bell, George Brown, Bobby Caldwell , Raymond Calhoun, Alfons Kettner, Robert Mickens, Kelly Price, Claydes Charles Smith (as Claydes Smith), Will Smith, Alton Taylor, Dennis Thomas, Starr Strukk & Ricky West (as Richard West |
 | 21. | 06/2000 | | 34
 | 44 US | 56 UK | | 12 R&B | charted as The Light / The 6th Sense in UK charts [MCA 155763] written by Bobby Caldwell , Norman Harris, Common (as Lonnie Lynn), Bruce Malament & Jimmy Yancey |
| 22. | 08/2004 | | 2
 | | | | 60 R&B | [Koch album cut] written by Bobby Caldwell & Alfons Kettner |
| Top 100 hits | 10 | 7 | 6 | 17 | |
| Top 40 hits | 3 | 4 | 5 | 7 | |
| Top 10 hits | 3 | 1 | 5 | 1 | |
| ✫ #1 hits | 1 | | 1 | | |
| US | UK | AC | R&B | |